


Now Brewing

by EverTheRenegade



Category: Supernatural
Genre: Alternate Universe, Bisexual Dean Winchester, Boss Dean Winchester, Boss/Employee Relationship, Castiel (Supernatural) Works in an Office, Crushes, Dating, Dean Winchester Works in an Office, Destiel - Freeform, Falling In Love, M/M, Seattle, Secretary Castiel, Slow Build
Language: English
Status: In-Progress
Published: 2018-09-01
Updated: 2019-06-16
Packaged: 2019-07-05 13:20:09
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 36
Words: 38,502
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15864429
Author URL: https://archiveofourown.org/users/EverTheRenegade/pseuds/EverTheRenegade
Summary: Castiel starts a job as the personal assistant to CEO Dean Winchester.





	1. Chapter 1

It was difficult to be bad at something like secretarial work. It was fairly simple, and he enjoyed the job. Taking calls, writing out emails, keeping things organized, and a personal favorite, putting people on hold. But perhaps the best thing about finding the work so effortless was that he could do it anywhere. And so he did.

Cas had started at the front desk of the local library in his small hometown as a Summer job. He found he had a natural knack for keeping things in order, for talking to people, offering direction or advice, and so he kept the job through the rest of high school. College had never appealed to him, so he took his talents and traveled with them. One letter of recommendation to the next, he had picked up jobs in vet clinics, doctor’s offices, car dealerships, anything he could find really, and he traveled, staying in places for as long or as little as he pleased. He had been beach side, had stayed in the mountains, spent time in bigger cities, until he found himself heading for Seattle, Washington. 

Some say Seattle has little to offer outside of the business market, the atmosphere dull and depressing, but Cas saw something different. Sure the place lacked a few days of sunshine, but he found the frequent cloud cover buzzed with not only the electricity of impending storms, but that of anticipation. He could feel it under his skin the moment he stepped out onto the sidewalk. This was a place without the dizzying nonstop lifestyle of New York, but the same sense of awe and excitement. 

Cas had come to Seattle after a position with a company he felt a particular reliance on. Winchester Roasters had fueled many of his long days behind a desk, giving his fingers the will power to challenge his own words per minute records, his hands the energy to pick up the phone before the second ring, and his eyes crystal clear blue to take in anything - or anyone- he might find of interest around his newest office venture. Company headquarters had been in the news for a scandal involving the leak of trade secrets, leading to the job loss of several lower rung employees who thought what they heard in the break rooms could never be tied back to them. And so, opportunity called Cas to the Pacific North West. 

Already having exchanged a few emails and phone calls with the HQ hiring manager, he made his way from his rental studio to the office building for a face to face interview. If this didn’t work out, he was confident he could find something else, but he wasn’t about to pass up the chance for an unlimited supply of the coffee that kept him going day by day. Cas had been frequenting Winchester Roasters since he was in high school, and it was one of the only constants he had as he traveled state to state, town to town. With his odd secretary jobs funding his addiction, there was no better way to bring his passions together. 

As he waited for appointment he helped himself to a black cup of coffee. Cas was partial to milk and sugar most days, but he wasn’t about to embarrass himself but lightening the color in his cup in a building full of connoisseurs. Taking a sip, he felt the coffee spill down his throat and spread warmth through his entire body. Face relaxing and eyes focusing on his surroundings, he mused that there is _almost_ no better feeling first thing in the morning. 

“Castiel?” A vaguely familiar voice asked from the doorway. As he looked up, a faint smile of recognition played across the redhead’s features. 

“It is so nice to finally meet you! I’m Charlie.” She took a step into the waiting area and extended her hand, glad to put a face to the name she had been speaking with for the last few weeks.

With the caffeine starting to bubble in his veins, he smiled enthusiastically, blue eyes wrinkling at their corners. Charlie, the Winchester Roasters hiring manager, had hit it off with him over many emails and a handful of phone calls, eager to bring him in and show him the place. She had admired his pages of work experience, as well as the enthusiasm he had for the company and his knowledge of the Roasters media presence. 

“Charlie!” Cas shook her hand, “I’m glad to finally be here.”

Charlie led Cas out of the waiting room, down the hall to her office. Upon walking in, he couldn’t help but smile. The office had a floor to ceiling bookshelf full of coffee mugs picturing characters from various comic books and movies.

“I try to combine my passions in my space.” She beamed, “I wouldn’t be here if I didn’t love coffee, hence the mugs, and I wouldn’t be me without all these characters influencing me as I grew up!”

Cas thought even if this job didn’t work out he would like to be friends with this woman. 

“Well I suppose that’s why I’m here too, isn’t it?” He said, taking a seat in front of her paperwork strewn desk.  
Charlie made a small attempt to tidy up as she sat, plucking Cas’s resume from the apparently controlled chaos. Cas noted, should he get this job, he would volunteer to file all her paperwork for her. 

The interview went smoothly, as Cas had been through the process many times. It certainly helped that he and Charlie had already become friendly, giving the situation a lighter atmosphere. She questioned his extensive experience, asking why so many jobs rather than something stable. He was used to this question, fully aware that his resume made him look like a flight risk. Fortunately, he knew a little something about schmoozing through it, his lopsided grin and bright blue eyes helping to clear any worry from his interviewers mind. Cas was a people person when he was working, talking to people was quite literally part of his job. Outside of professional relationships was a different story. And, he reassured himself, if this place didn't work out, there was always another opportunity just ahead. He would be itching to travel somewhere new soon anyway.

***

As the interview progressed, Charlie became more sure this was the perfect person for a very certain position. She casually questioned Cas on what he knew about the recent scandal. To her relief, his details were fuzzy in all the right places. She didn't tell him he would be filling the position the company traitor, Benny, had filled as Mr. Winchester's personal assistant. That was basically a step up from a run of the mill secretary position. Charlie's job had been difficult over the past few months after the news had come out, struggling to find someone as trustworthy, driven, and likeable as Benny had been. He had hurt them all when he sold off their company secrets for a bigger paycheck, but none so much as their CEO and his best friend, Dean Winchester. Getting to know Castiel over these last few weeks, and now in person, she was confident he could replace Benny, and maybe even restore Mr. Winchester's faith in himself as the head of the company.

Conversation and questioning subsided, signaling the end of the interview. Cas would never let it show, but this part always made him a little nervous. Charlie chewed thoughtfully on her lip, wondering if she should share more about the position or leave it on a need to know basis. Castiel seemed perceptive enough, and she didn't want to overstep her bounds by sharing what the media didn't even know. With an exhale, she stood and smiled, extending her hand.

"So can you start tomorrow?", she beamed.


	2. Chapter 2

Dean Winchester sat at his desk, staring out the window into the usual Seattle cloud cover, mindlessly rolling a balled up piece of paper in his fingers. The idea that he was being a little dramatic, even after months had passed, briefly crossed his mind. He was unmotivated, always aware of the empty desk that sat within eye shot of his own, and the looks the scattering of other office employees gave him each morning when he walked in. He scoffed, _more like all the employees in this damn building_. He felt guilty, betrayed, hurt and angry. They were best friends, this was his life's work, and for someone so close to him to do this, to use him-

His self loathing train of thought was cut off by a quiet knock on the office door. He could see Charlie's red ponytail bobbing out of sight as he caught her peeking through the adjacent frosted window. Dean chuckled, dragging himself up and tossing the paper ball into the nearby trash can, thinking he was thankful not everyone close to him was as big an asshole as Benny was.

"Good morning Mr. Winchester" Charlie smiled as he opened the door. Dean rolled his eyes.

"I hate that" he said as she strode into the office, a smirk playing at her lips. Charlie and Dean had met in college, bonding in their business classes over their similar taste in nerdy things. When he and his brother had inherited the company after their father fell ill, Dean knew he wanted Charlie with him every step of the way. At least she had remained loyal.

Shaking the negative thoughts from his head he shut the door and followed her to plop down in the armchairs beside his desk. The Tasting Corner, they called it, the place where they sat to try new products before anyone else even knew they existed. Dean had only allowed a select few trusted employees to enjoy this spot with him, in front of a large window looking out over the city. _A mistake,_ he thinks after a moment, _I should have kept it all to myself_. 

Charlie pushed a folder into his hands. "I found someone. He starts in the morning."

Dean groaned, throwing his head back dramatically, not even bothering to open the folder.

"Oh stop it," Charlie said, shooting him a glare ,"not every guy is out to break your heart. Besides, who is to say a pretty little lady sitting out there couldn't do the same?" She waggled her eyebrows and smirked.

It was Dean's turn to glare now, the only way he could think to handle his discomfort with this topic, even if nobody else was around to hear the conversation.

"That has nothing to do with it" he mumbled, casting his eyes down to the folder labeled _Castiel Novak_. "This is about trust and.. And professionalism and.. Business.." He trailed off, acutely aware that Charlie was watching him through narrowed eyes.

"Do you trust me to find someone perfect for the job, Dean? Or would you rather I take in date applications? This guy is good. He has the experience, he has the passion, and he is a fresh face with no idea about your personal life. You said it yourself, you have to keep them separate. You’re his boss, you're everyone's boss! Don't let anyone think otherwise. We can deal with your other shit outside the office, okay?"

Dean chewed the inside of his cheek. Charlie was right, she was always right. She knew this company just as well as he did, she knew who fit in and who didn't. Last time had been a mistake on his part, but it wasn't going to happen again. He was the boss, dammit, it was time to stop sulking and run a damn business.

He sat up straighter, setting his jaw, and met Charlie's eyes. "Thank you, now tell me about my new personal assistant."


	3. Chapter 3

Cas arrives in the Winchester Roasters lobby at five to 8, where Charlie is waiting to show him to his desk and familiarize him with the building. At the front desk he is introduced to Donna, a bubbly blonde woman directing anyone that might walk through the front doors. Around the corner in the security office they say hello to Jody and Alex. At the elevator, Cas meets Adam, the solemn mail room manager waiting to catch a trip downstairs. Charlie seems anxious as the elevator dings at each new floor, and it Cas cocks his head to the side realizing the button for the seventh and topmost floor is highlighted. His experience and job title had always kept him closer to the ground, dealing more in the customer service and paperwork realm than working as a personal assistant. He turns to Charlie as another ding signals their arrival, and she smiles, stepping out ahead of him onto the office floor.

Giant picture windows surround him, dousing the entire floor in a soft glow as the morning sun struggles to rise above the Seattle cloud cover. To his right, along the outer wall are a series of desks designed to be shared in a similar fashion to a computer café. To his left, three long tables with bar seating stretch parallel to a couple glass enclosed meeting rooms. A few lazy morning smiles turn to greet the pair as they walk to the other side of the floor, between the desks and tables. While personal belongings are strewn across most of the desk spaces, it seems all present are gathered around the long tables, talking quietly, coffee cups clutched in their fists.  
Well, they were talking quietly. Now it seems all eyes are on him.

"Hello!" An enthusiastic voice calls from the left, and Cas lifts his eyes to see a tall, bright eyed blonde striding around the table to greet him. "You must be the new guy! Honestly I am so glad, I was rather bored of carrying that title myself." He reaches his hand towards Cas, "Balthazar."

"Cas." He states, giving Balthazar's hand a firm shake, nervous suddenly under the gaze of literally every person in the room.

Charlie steps up beside him, "Balthazar is our newest addition to the PR team, and a fun source of entertainment for the whole office." This earns some chuckles from the rest of the room, as Balthazar rolls his eyes. 

"Well it has been a pleasure to meet you Cassie. From one new guy to the next, just call if you need anything!."  
And with that he turns on his heel, snatching his coffee off the table and heading toward the elevator. At that the rest of the team starts to move, some heading for the desks as others hurry to catch a ride with Balthazar. Cas's watch is nearing 8:30 as he and Charlie continue toward the far end of the floor.

"So most department head's have a desk up here to be closer to Mr. Winchester if they need it, but usually prefer to hang around their department's on the other floors. Balthazar is just the floor below, but the PR manager, Gabriel, can usually be found up here." She gestures then at the desk they're passing, a bowl of candy nestled between a laptop and a stack of papers.

"And this is you!" She beams, stopping next to the desk furthest from the elevator. Directly behind him is what looks to be more office, frosted glass panels flanking a dark wooden door. A door with an inlayed plate labeled D. Winchester. Cas turns to look at Charlie, blue eyes going wide.

"Charlie this is a secretary job I applied for, correct?"

"Well… I mean yeah essentially. Secretary, personal assistant, that's basically the same!" Cas opens his mouth to speak but she cuts him off. "Okay you just had so much experience! And Mr. Winchester needs someone like you. He needs someone who knows what he's doing, and out of all the people I have interviewed you were the only one who seemed genuinely interested in the position and the company. It doesn't seem like this is just a job to you… it's skill and it's a hobby and you enjoy it. That's what De- uh, Mr. Winchester needs."

A sudden flurry of movement behind him distracts him from voicing his concerns. He turns to see the office in a state of hustle and bustle it had not been in moments before, and as he scans the room he realizes why. Striding down the center isle, jaw set and brows furrowed is the man that inherited this whole operation. He nods curtly at each of his employees as they bid him a good morning, making a beeline for where Cas stands, staring. Cas turns quickly, trying to seat himself and get organized in the approximately 10 seconds before Dean Winchester would be in his presence.

This was a very important business man, someone whose business practices, mission statement, and face were admired by people world wide. And now, Cas had the responsibility to… to, what? Not screw it up like past employees had? Maintain his reputation? Make sure he got his coffee in the morning? No, he was in the coffee business, he had to get his own coffee. Did he? Was this Cas's job now? Never in his life had he doubted his confidence in his job, it defined him, this was who he was. But this was different, and he felt all too warm as a wave of nerves flooded through him. 

"Okay" he heard Charlie exhale, and he stood ready to greet his new boss. Nervous as he was, Cas forced a small smile, but Mr. Winchester was not slowing down. He opened his mouth to speak and-

"Charlie," the CEO nodded, shifting his gaze ever so slightly to Cas, "Secretary." 

And Mr. Winchester continued right into his office, door closing with a click behind him.


	4. Chapter 4

Dean had given himself a pep talk as he got dressed this morning.

_I'm the boss. I run things here. I can be stern, I can put my foot down, I don’t have to open up to anybody. I'm Dean fucking Winchester. I'm the boss._

Dean fucking Winchester felt good about finally having a new personal assistant after a solid night's sleep and an espresso to get himself out the door. But then he got to the office.

"Good morning Donna" he called as he walked through the front doors.

"Oh hiya, boss! Say, I met your new guy today, seems like a good kind of fella!" She had replied, all smiles and bright eyes.

His steps faltered a little. So the guy was going around making friends already? Why couldn't he just be the quiet, keep to yourself type? They didn't need another friendly face to hurt them all down the road. He just needed someone that could do his work and go home.

Dean rounded the corner to see Gabriel step into the elevator, and hurried to catch the ride up with him. Seeing Dean's thoughtful expression, he raised an eyebrow. "Worried about the new guy?" he asked, ever perceptive. Dean sputtered, annoyed that everyone knew him well enough to read him so easily. Maybe that was his damn problem.

"Not at all" he brushed off, "he's just a secretary."

Gabe's still arched eyebrow implied he didn't buy it, but he wasn't going to pry. Not yet, anyway.

The door opened at the sixth floor, and conversation drifted in.

"Cas, his name was. Didn't say much, but he looks like a good bit of fun. And I think Big D will like the new scenery as well." comes Balthazar's voice, followed by a few chuckles. Gabriel raises both brows now, chancing a quick look at Dean before stepping out of the elevator.

Left alone to feel his cheeks flush, he decides Dean fucking Winchester needs to be more of a boss and less of the charismatic friendly face people around the office seem to see him as. No more mister nice Dean he thinks as he exhales. He sets his jaw, elevator doors opening to the seventh floor office penthouse, and steps out.

A quick scan of the room spots Charlie's fiery hair at the far end of the floor next to his office. Beside her, a tall dark haired man in a purple button down under a white cardigan. As he strides toward his office, he nods curtly to each greeting, keeping his eyes trained on the pair at the end of the center isle. Dean watches the man jump into action, nearly tripping over his desk as he tries to get behind it. Charlie had said Castiel was professional and confident, but this guy seemed to be a nervous wreck. 

Dean gave them both a quick nod as he closed in, "Charlie, secretary," and continued straight into his office.  
As he heard the door close behind him, he exhaled, letting his shoulders drop and jaw unclench. He didn't enjoy being the stern boss man this was going to turn him into, but be knew it had to be done for the sake of the company. And his sanity.

He slung his suit jacket over the back of his chair, hearing Charlie's nervous babble vaguely through the door. The frosted glass allowed him a rough picture of what was happening, taking note of the way Castiel was sitting hunched over with his head in his hands, and Charlie leaning over him. 

_Hopefully she isn't telling him I'm not always like this,_ he thought, turning his gaze to his awakening computer screen. Seconds later, his door opened and shut, and be looked up to see Charlie glaring, arms crossed over her chest.

"Uh, what the hell dude? This guy is a nervous wreck and you couldn't even give him a warm welcome? What's going on?"

Dean cleared his throat, sitting up a little straighter as he typed in his password. "I thought you said he was a confident professional. He doesn't need a job introduction" he replied coolly, not lifting his eyes from the screen. Charlie was one of his closest friends, but this was work, and if needed to take his job more seriously than so be it.

When the seconds ticked by without any response, however, he looked up. Charlies glare had turned into narrow eyed scrutiny as she processed what he said began putting the pieces together.

"You can't fool me, Dean. You think turning into a stone cold CEO is going to change what happened? Prevent it from happening again? Your employees, your team, loves you Dean. That's how you built Roasters into something this great. Don't push people away. You're the reason they love coming to work every day."

He sighed, "People already like him Charlie, already interested in another friendly face. Last time it was too good to be true and look what happened! Too easy to trust…" he trailed off, lost in his own mistakes. Speaking of, "And I heard some talk about me liking him as well! I can't let that kind of crap go on here! I'm your god damn boss, not a gossip topic!" He hadn't realized he had raised his voice, or that he had stood up, until Charlie's expression became one of concern. He cleared his throat, slowly falling back into his chair.

Chewing thoughtfully on her lip, she let out a sigh. "Well, Mr. Winchester, you know what is best for this company, and your team will always have your back. But if you need a friend, I'll be in my office. See ya, boss."

He's not sure how long he sat there in thought after Charlie left, staring blankly at the closed door.

They're all pretty friendly in this office, and when this whole incident went down, that had been Dean's biggest regret. Benny had been playing them all, flashing his smile and charming everyone with his heavy New Orleans accent. Nobody had suspected he was here for information, to turn around and betray the team that had grown to love him. The media flashed a story of loose lips in the break room, some chatter amongst employees that got into the hands of some no good people, but nobody knew the real story. Nobody knew just how close he had become with his personal assistant, or just how much Dean might spill to someone he thought he could trust. Someone he thought his was falling for. Or at least, he thought nobody knew. Again, it seems he was too easy to read within his own office. He scrubbed his hand over his face with a groan, thankful that his remaining employees respected him enough to keep his personal life out of this. 

Never again, he thought. No more getting close to his employees. No more blabbing his mouth off late at night after one too many beers. He wasn't going to put everything he had worked for at risk, not ever again.  
Exhaling, he squared his shoulders and clicked to open up his email. The phone ringing to his right gave the final jolt to break him free of his thoughts.

"Yes?" His office phone was a private line, anyone calling needing to first get patched through by his-

"Mr. Winchester" a voice like a deep rumble of thunder came across the line, "your - uh - the other Mr. Winchester -uh, Sam, is on the line for you. Shall I patch him through?"

Dean swallowed thickly, eyes flitting between the shadowy figure sitting outside his office holding a phone to his ear and the blinking call waiting button on his desk. He watched the figure turn slightly as if to glance into the office, and Dean shook his head, clearing his throat and the dazed feeling from his mind. 

"Yeah - uh, yes. Please. Thank you."


	5. Chapter 5

Cas hadn't been all that confident the first time he sat as his new desk. As the week progressed, however, he found he knew the work and fell back into a familiar routine. The difference was the ever looming presence of his new boss. Of course they had spoken sporadically, Cas was his personal assistant after all, but Mr. Winchester maintained his distance, seemingly unwilling to familiarize himself with his new employee. 

Thinking it over to himself back at his studio later in the week, Cas guessed that the man's behavior made some sense. He was the CEO of one if the greatest businesses of modern day. He must have to keep a professional atmosphere about himself to maintain his image. _Apparently professionalism is synonymous with being a total dick_ , Cas smirked. 

It wasn't really that he was being a dick, Cas had observed, but more like he was put off. Nervous even. Mr. Winchester rarely looked at Cas, fleeting glances in passing if that. His expression looked worried, his brows usually furrow, a frown tugging at his lips, fists clenched at his sides. Cas wasn't sure why his boss would be angry with him, he had done nothing wrong in his first week on the job. In fact, several other employees had given him praise. It's not like the job was difficult, but it seemed like Cas holding the position was something to be admired in itself. He had tried asking the others around the office about the behavior, and was usually met with a few smirks, knowing glances. Charlie had promised things would get better between them, he was just having a rough time after the whole info leak things.

By Friday morning, Cas had made up his mind to do some light digging, and maybe a little brown nosing. He made sure to get to the office early, nodding a friendly hello to everyone else that had the same idea. While they clustered around the usual tables discussing plans for the weekend- tasting tables, he had learned - Cas wandered to the floor brewing station and began fixing a cup of the piping hot dark roast for Mr. Winchester. It had been a long week, and what better way to start his boss's weekend then with a cup ready for him to get right to work.

He had learned this past week that Mr. Winchester liked all priority paperwork set up in his office before he arrived, which was usually about a half hour after everyone else. "He likes to jump onboard when the engine is already running" Gabriel had explained. From Cas's understanding, Mr. Winchester and Gabe were friends outside of work, having met through the other Mr. Winchester, Sam.

So, one could imagine Cas's surprise as he pushed the office door open, hands full of coffee and paperwork, to find Dean Winchester in the process of pulling a sweat damp t-shirt over his head.

"Oh, shit - uh - shoot" Cas stammered, half turning to walk back out the door and half reaching to put everything down on the desk.

"Jesus, man, what the hell!" Dean yelped, using the wadded up shirt to cover his torso.

"I- your paperwork - I thought - and coffee -okay, shit" Cas was trying to look everywhere but the half gym clothes clad Winchester Roasters CEO glaring at him from the corner of the office. He noted, vaguely, the bathroom door over there he hadn't noticed before, and all but sprinted out to his desk.

Naturally, everyone around the tasting table was turned, looking for the source of the sudden commotion. Balthazar was sporting an ear to ear grin. 

"He, uh, runs to work on Fridays" came Gabriel's voice, his smirking face poking out from between other amused employees. 

Cas felt his face flush at his failed, and frankly embarrassing, attempt to get on his boss's good side. Without a word he fell into his chair, putting his head in his hands. It was just a minor screw up, and how was he supposed to know anyway? He was just doing what he had done every other day this week, there is no way Mr. Winchester could be angry at him. Right? 

Scrubbing his hand over his face, he sat up straight, flipping open his desk planner and booting up his computer. The others had gone back to quiet conversation, except for Balthazar who was heading toward him.

"So did you see anything good?" He asked, waggling his eyebrows suggestively.

"What? No oh my god no! Why would you- he's my boss!" Cas supplied, Balthazar's expression unchanging. Cas gave an exasperated sigh and turned his attention back to his laptop. He wasn't going to let this phase him. At least not while he was still at work.

Balthazar cleared his throat, not one to be ignored "Well, Cassie, the few of us will be finding a happy hour later, and I would love for you to join us. Maybe you'll be more inclined to share with something fruity in you." He said with a wink before turning to whisk Gabe away to the elevators. 

Cas let out a long breath, blowing some of his unruly hair off his forehead. Hopefully the rest of the day would be uneventful, and maybe catching up with some of the team outside of the office would give him a chance to gain some insight on Mr. Winchester. _As if I haven't gotten my Winchester fill already,_ he thought.


	6. Chapter 6

He made no moves to leave the office for the rest of the day after this morning's incident. On Fridays, Dean would run the blocks to work rather than going to the gym. It was a nice way to start his weekend, and gave him the little burst of adrenaline to get through the day. His office had a nice ensuite bathroom, equipped with a small shower and closet. Sam had told him that before the company bought the building, the top floor was intended to be a penthouse suite. Plumbing already in place, they decided to make use of it when the plans changed to an office suite. Dean took full advantage, despite Sam telling him it was 'weird' to shower at work. It had never been an issue. Well, before today it hadn't.

While he had been flustered at first, he laughed about it while he rinsed off. He had no doubt that come lunch time, it would be the highlight of everyone's day. Still chuckling to himself, he rolled his sleeves to his elbows, forfeiting his suit jacket in leu of a self proclaimed semi-casual Friday, and made his way over to his desk. By now the coffee was lukewarm, but much appreciated to reel his mind back into work mode. He chanced a glance toward the door, making out the figure of Castiel sitting at his desk.

Should he go say something? Apologize, or tell him not to worry about it? How was the guy supposed to know, anyway? He kicked himself a little, knowing full well that had he been his usually friendly self this week, this could probably have been avoided. After all, the guy was just trying to be nice. He was probably trying to offer the coffee as a olive branch for a tension Dean himself had started. Maybe being this stern guy wasn't the best course of action. Castiel was his personal assistant, they should at least be kind of friendly, right?

Dean sighed, unsure of himself for a brief moment. He didn't want to make the new guy feel awkward, but that ship might have already sailed. But if he didn't say anything at all, was that worse? He had no idea. This was just a secretary, it shouldn't matter so much.

Eyeing the stack of paperwork Castiel had hurriedly thrown on his desk, he saw the topmost one was packet from Sam containing the regional information about their newest coffee farming location. His brother had inherited equal parts of this company from their father, but Sam had always been the more out in the field doing research type, and so he spent most of his time traveling. He had close relationships with their network of coffee farmers, and liked to scope out new locations and beans and techniques. While Dean was the face on Winchester Roasters business end, the company would not have grown to what it was without Sam.

Earlier this week Sam had called about the new farming location this packet covered. A small valley in the mountains of Guatemala boasted a limited but refined supply of bean, and Sam had been thrilled at the prospect of offering something of such high quality. Not that their other farms didn't produce high quality product, but the small size and unique location of this farm was something different entirely. What Dean flipped through now was essentially a research paper Sam had put together about this little farm.

"Nerd" Dean smirked, shaking his head. The kid was passionate and thorough, and nobody did better research.

He started up his computer, setting up to type out an email to Sam, and took another swig of the quickly cooling dark roast. As his computer blinked to life, Dean mulled over the idea of going to say something to Castiel. He just couldn't bring himself to make more of a scene for the guy after what Dean is sure Balthazar put him through earlier. Whatever, the guy was probably over it. Just a little mishap, no harm done, they could get on with their lives.

He set to work on his email.


	7. Chapter 7

Cas had spent the day checking over his shoulder, making sure Mr. Winchester was not looming behind him with a soul piercing, green eyed glare. Every once in a while, he looked up to see another office employee watching him with an amused grin. The clock seemed to slow down with each hour that passed. Fridays were apparently slow, nobody wanting to bother the CEO so close to the weekend. At this point, downing a couple drinks sounded more and more appealing. Anything to push the embarrassment out of his head, and make less obvious the flush that rushed to his cheeks every time he thought about it.

Balthazar's comment had not made it any better. Did he come off as gay? Not that he cared if he did, but that might have made Mr. Winchester even more uncomfortable. He paused at that thought, wondering if perhaps that was what made the man so stand offish. He shook his head, there was no way this guy could be a homophobe, not in this office. Maybe it was the whole _personal_ assistant thing, maybe he was more accustomed to some tiny little thing in a short skirt taking up residence outside his office, maybe he didn't like not having the eye candy, the options…

Cas smirked to himself, _options_ were limited with those big glass windows.

His own stupid joke lifted his spirits a little as he tried to focus on getting through the next few hours. Usually Mr. Winchester made an appearance around lunch time, but as the hours ticked by, nothing changed. Cas had taken to bringing along his own lunch until he familiarized himself with the area so as to not get lost on his lunch break. Or get caught eating alone. 

Despite his friendly attitude toward the other employees, he had yet to establish an outside of work relationship. Granted it was only the first week, and tonight he had agreed to go out for drinks. He also understood the employees being apprehensive to trust him as a new guy in light of the recent scandal. Hopefully tonight would change that. 

As the upper floor emptied out for lunch, Cas sat back in his chair and pulled out a peanut butter and jelly sandwich. Usually he would venture down to the small office cafeteria for a change of scenery, but that was only if Mr. Winchester had already taken his leave. Afraid to make any more mistakes today, he stayed close by in case he was needed. Taking the last bite of his sandwich, he got up and strolled over to the floor to ceiling windows that made up the wall on the right side of the building. Some early afternoon sun was poking through the clouds, giving a rare view of the city. He smiled at the prospect of exploring this weekend.

Cas was pulled from his daydream by the sound of a door opening behind him, and he turned to see Mr. Winchester stepping out of his office.

Usually the man wore a suit jacket and pants over a light colored button down, the usual outfit of a big deal CEO. In the last five days, Cas had not seem him in anything else, actually. Now, however, the usual jacket was missing, his crisp white shirt rolled up to his elbows, the top couple buttons undone. Briefly, Cas wondered if the earlier mishap had flustered the man into not getting fully dressed. 

"Hello" Cas said before he could stop himself, not sure if he should alert Mr. Winchester of his presence or hope he could remain invisible in his sunshine filled corner.

Dean jumped, turning toward the voice, his eyes catching the sunlight, a twinkling candy apple green. "Oh, uh, hey man. I didn't realize you were still here." He reached up to rub the back of his neck. "Not taking a lunch today?"

Cas wondered if he was gaping, because if his boss hadn't realized he was gay before, this had to be a dead giveaway. Who didn't love a man in some loose, business casual? 

He cleared his through, bringing his voice back down to his usual gravely rumble, "No, uh, yes. I ate already." He gestured uselessly towards his desk, where an unopened bag of chips still sat. Whatever.

Dean smirked, and Cas let out a quiet breath.

"Okay then. Well, uh, sorry about this morning. Well, not sorry, um, I mean sorry nobody told you. Sorry I didn't tell you. It's no big deal though, it's not the first time and-" Dean cut himself off, his cheeks turning the slightest shade of pink and he brought his eyes back to Cas, who was still standing there staring. He cleared his throat, "Yeah, okay, anyway, thanks for the coffee."

A small smile tugged at Cas's lips as it became evident that his tough guy boss was, in fact, not so tough. _This can be saved_ , he thought as Mr. Winchester turned to leave.

"I can do that again if you'd like" Cas said, and he watched the pink in Mr. Winchester's face deepen a shade before he realized what he'd said. "Oh my god, the coffee! Not the - no, the coffee." Cas scrubbed a hand across his face, stifling what was half a laugh, half a groan.

Mr. Winchester turned back to him then, and let out a laugh of his own, forcing Cas's eyes back to his boss. Cas let out an apprehensive chuckle of his own. This was good, right?

"Alright man, sounds good. Thank you."

Mr. Winchester still had a small smile on his face as he headed toward the elevator.


	8. Chapter 8

Charlie nudged at Dean's elbow as they lounged together, sharing a plate of fries. Years ago Charlie had started the French Fryday tradition, which had encouraged Dean to start his Friday morning running routine. Maybe it was counter productive, whatever, they had fun.

"Hello? Are you gonna spill?" She asked, mouth full of fries.

They were securely locked away in Charlie's office over their lunch break, where Dean had intended to give her a play by play of this morning's post-run incident. Now he had the addition of what only occurred moments earlier, Dean making a fool of himself in front of this guy he had been actively trying to intimidate.

He sighed, sitting up and reaching for a handful of fries. "He was just doing his job, nobody had warned him that I would be in there. At least he didn't catch me as I was getting _out_ of the shower" he mused, shoving the fries in his mouth. He had a lazy grin on his face, and Charlie definitely noticed.

"You like him." She stated plainly, sucking the salt off her fingers before going in for more.

Dean opened his mouth to protest, but with one look and a raised eyebrow, Charlie cut him off. 

"Alright, alright. He's a good looking dude, I can't deny that. But I'm not getting into that crap again, you know that. I just can't. Besides, I don't even know him." He wouldn't meet her eyes as he reached for the last bit of fries. She knew him too well, but she would never tell him how to live unless he was being an idiot. In this case they both knew he couldn't take any chances, not again.

"So… have you heard from him?" Charlie asked, cautiously.

Exhaling, Dean turned to look out the window. After the initial leak of company trade secrets, Benny had directly contacted him to confess, but also bribe him. He had told him everything, his plan from day one, coming in to be a mole and sell any information to the highest bidder. What was never a part of his plan, however, was the secret relationship he had started with his boss. Despite the way they felt about each other, their positions made it difficult to bring the relationship to light without causing a scandal. Instead, a different kind of scandal had come out of the whole thing. Benny was smart and had directly contacted Dean because he knew he couldn't let his reputation be tarnished. He couldn't admit to the world that he, the CEO of Winchester Roasters had been the one to give up so much of that information under the guise of love. Benny had dealt a blow to the company, sure, but they could recover. If other businesses utilized their trade secrets, so be it, they would never be the same company, they couldn't compete.

But then Benny threatened Dean. Threatened to go to the media and give them _the full story,_ unless Dean could compensate him for keeping his mouth shut. He had been heartbroken, this wasn't the man he had fallen for. But after losing his partner, he couldn't bear to lose his company, his friends. And so he caved, giving Benny the money he asked for, and Benny had kept his word. It had been months and now Dean was prepared to deal with the consequences should he decide to go back on his end of the deal, but until then, he had go just hope for the best.

Afterward, having drank potentially the entire contents of his personal liquor cabinet, he had called Charlie. Sam, in Costa Rica at the time, had made his second trip back to Seattle in that same month the next morning after Charlie had gotten in touch with him. The first trip after the initial leak had been all business, and Dean had done all he could to steer the rumors away from Benny and toward 'a group of interns' in hopes of preventing Benny coming forward. The second trip was for a near incoherent Dean to explain everything to his little brother, in hopes of finding a solution. It was Sam who told him the best plan of action was to keep moving forward and hope for the best. Months later, and Charlie and Sam were the only people who knew the real story.  
Neither of them knew that Benny had been sporadically contacting him. Nobody knew.

"Nope" he sighed, playing the hurt but dealing with it demeanor he had mastered. "I doubt I ever will. He got what he came for, none of it being me."

Charlie's eyes flashed with worry, and she got up to toss the empty tray of fry crumbs.

"Well…" she said slowly, turning back to him with a hopeful expression, "Balthazar is planning on bringing Cas out for drinks tonight if you think you can drop the big bad CEO persona and want to come along."

_Cas, hmm,_ he thought, testing the nickname in his mind. "I don't know Charlie, depends how the rest of the day goes. If it's anything like this morning, I might be so emotionally drained I'll sleep through the weekend." He flung a dramatic arm over his eyes with a grin.

She swatted at him, "Oh whatever, you'll come out eventually", waggling her eyebrows at her double entendre.

Dean rolled his eyes, hauling himself up to head back to his office.


	9. Chapter 9

Cas followed the throng of Winchester Roasters employees to a restaurant a few blocks away. Purgatory was a company favorite, especially Mr. Winchester's, Charlie had told him. It was their usual Friday happy hour spot because of their huge beer selection, but Dean apparently swore by their burgers. Part of Cas hoped that meant Mr. Winchester would be joining them, but he had stayed behind at the office to finish some things, sending the rest of them off at 5 sharp.

The bar staff cheered a greeting at the group walked in, finding their way to a series of booths toward the back of the building. Balthazar was quick to slide in across from Cas, followed by Aaron, a part of the tasting team. Charlie was off mingling with the others, and so Balthazar wasted no time. 

"So, Cassie, how are you liking it here?" He asked, flipping open the drinks menu, brows raised questioningly.

"I'm still trying to get acquainted with the area, and the office, but I am enjoying the work." Cas replied, his usual rolling thunder voice raised to be heard over the noise of the Friday afternoon crowd.

"Oh I think you're plenty acquainted with the office, right?" Aaron interjects, nudging Balthazar enthusiastically, a laugh rising between the two of them.

Cas feels his face flush, but he lets out a laugh, trying not to let the embarrassment get to him. "Yes I suppose you're right, but I wouldn't mind seeing some more" he raised an eyebrow, playing into the joke. Might as well.

His booth-mates both choke at that, hesitating before bursting out laughing, and Cas smirks.

The waitress makes her way to them, and Balthazar orders a round of drinks called Mojo for the three of them. As expected, they are a fruity and vibrant blue, served in a glass shaped like a large vial with a silver metal straw. A sweet blue raspberry flavor with strong enough alcohol content to have you squinting your eyes with each sip. After the third of which Cas decides it actually tastes pretty good.

With the confidence of his Mojo, Cas starts to dig.

"So, Charlie says Mr. Winchester isn't always so stern. Is it just me or is there more to this?"

Balthazar rolls his eyes, "Oh call him Dean. Not to his face of course, unless he says you can. Nobody calls him Mr. Winchester." He pauses to sip his drink, "But the big mean boss thing has been recent. We think it has to do with the whole 'scandal' thing" he finishes, waving his hand dramatically when he says 'scandal.'

Cas raises an eyebrow questioningly while taking a sip, and Aaron looks around cautiously.

"Okay, so the guy made a big deal about this whole information leak. Company secrets, the stuff that sets us apart from the rest. It was a shitty blow, but it wasn't like the stuff was kept under lock and key. It'd basically common knowledge around the office! But, it's also common knowledge that stuff doesn't get discussed outside of the office." Aaron shrugs, looking around again before continuing. "I think it's safe to say that, even so, we've all talked about it to other people. But who cares? What's weird is that the guy apparently confessed, yet nobody has heard his name outside our little building."

Cas looks at Balthazar for more, but the man is paying very close attention to the way his straw moves through his cocktail. Turning back to Aaron, Cas says "What do you mean guy? I thought it was just some young interns or something?"

At this, Balthazar looks up, abruptly cutting off the conversation with one look as Charlie nears the table. Quietly, he turns to Cas and says, "This little chat will have to continue at a later time." Cas narrows his eyes, wanting to know more, but Balthazar turns then to the approaching Charlie and grins, welcoming her into the booth. He sends Cas another quick glance, urging him to drop it for now.

***

After a few more doses of Mojo, Cas felt much more at ease with his new coworkers. They had swapped stories of office mayhem, travel, and the occasional reference to last year's holiday party without further explanation. Balthazar discovered Cas's rental was not far from his apartment and so they decided to catch an Uber back together.

In the backseat, languid conversation turned serious, and Balthazar quietly went into explanation of their earlier conversation.

"This is not at all common knowledge around the office, Cassie, and so I beg you keep it to yourself. I'm sure all will come out in due time, but be patient." Cas nodded sleepily, Balthazar shifting in and out of focus in the seat next to him. It had been a while since he'd been out drinking.

Balthazar took a deep breath, "It was not, as the media said, some idiotic interns, but one man that had been a friend to everyone. From what I have gathered, he had gotten the job with the sole intent of finding information he could sell. He worked there for near a year, becoming friends with everyone in the office, including Dean. You are the first person to fill his position since he left the company months ago."

Cas processed this, eyes narrowing as he wrapped his head around the new information. Out the car window, he recognized they were nearing his place. "So… why did the news lie?" He only slurred a little.

"Well, that's the biggest mystery of all." Balthazar continued, eyes gleaming with suspense, "I can't be sure as I was hired shortly after this whole mess, but from what I have heard, Dean had given the media a twisted story." The car pulled over now, but Cas was still confused.

As Balthazar leaned across Cas to open the door, he whispered, "Dean didn't want the media to know he was sleeping with the guy that had sold his company secrets."

Cas stumbled out of the car, squinting as he tried to understand these snippets of information he had gained over the last few hours. Balthazar yelled to him as the car pulled away, but he only vaguely noticed as the pieces slowly came together. As he trudged up the steps to his front door, he twisted the key, and everything slid into place with a click.


	10. Chapter 10

Weekends were hard for Dean. Everything feels lonely when you've become so accustomed to having another presence around, only to have it ripped away in an instant. What might be worse is that recently, that familiar presence had been nosing it's way, infrequently and randomly, back into Dean's life.

Weeks after Benny had called to blackmail him, after which he proceeded to drink himself into oblivion, he had taken a weekend trip down to Portland. _Land of craft beer and coffee houses_ , Sam had promised him. His brother, always rather perceptive to Dean's inner demons, had been dropping subtle hints about taking a break to clear his head. It was that weekend he decided to let himself live a little, and wandered into an inconspicuous gay bar, hoping to catch some tail and well, _clear his head._

He had been eyeing the bartender, as well as the couple of ladies sitting at a high top on the other side of the bar, and man were they eyeing him back. _That_ could be a lot of fun. But then he felt the hair on the back of his neck stand up, that feeling that he was being closely watched, and he spun around to meet a pair of all too familiar eyes. Dean froze, color draining from his face and eyes going wide as Benny glanced around the bar before sliding from his own table to approach Dean.

He didn't know if he should scream or run, throw a punch or burst into tears. 

Settling into the chair beside him, Benny's unmistakable southern drawl reached his ears, "You don't have to stalk me, you know. A phone call would have worked." He smirked at Dean, trying to ease the air.

Dean wasn't having it.

Through gritted teeth, Dean mumbled, "I'm on vacation, I'm not stalking you. I figured you'd have hit the east coast by now."

Benny was never one to be put in an awkward situation. He could make any topic, not matter how tense or hurtful, into a lighthearted conversation. 

"Nah, not me. There's a whole coast right here full of cities with… opportunity." He flashed Dean a grin then, causing his stomach to churn with a little bit of butterflies and a little bit of disgust. His gut told him to drop the bartender a twenty and haul ass back to his hotel, back to Seattle even. But at the same time, the familiarity of sitting next to Benny at a bar, his subtle smell, the way his voice rumbled in Dean's chest… he didn't want it to go away.

With a sigh, Dean caved. He would never have been able to properly enjoy himself this weekend and he knew it, so might as well settle for something close to an old friend. 

That's what Dean had let himself believe anyway, but a couple hours and quiet a few beers later, they were stumbling through the door of Dean's hotel room, desperate to make up for lost time, to gain closure maybe, to take out all the pent up emotions that had been bubbling under their skin. Dean wasn't sure if the relationship he had with Benny had been real or just another means of getting information, but this felt pretty real. Dean could give him nothing else, and so maybe what he wanted this time was Dean.

Come morning, Dean would kick himself for thinking something so ridiculous as he woke up alone in his hotel room.

Benny never changed his number, and Dean couldn't bring himself to delete it. So in another couple weeks when he got a text, he was kicking himself again.

He chalked it up to Benny knowing Dean's true feelings and using him for a good time, but Dean never gave in. Not yet anyway. Every _'hey pretty boy, you around on Saturday?'_ made his heart skip, but he wouldn't let himself respond.

And so, that is where Dean had found himself this particular weekend, knowing full well he could be having a good time, but locking himself in his apartment with some beer and a couple movies instead. Occasionally he pulled out his phone, stared at the text from Tuesday, and toyed with the idea of answering before tossing it to the other side of the couch. Scrubbing a hand over his face, he let his head fall back onto the couch and forced his mind to go over this past work week. There was all the new research Sam had sent him that he needed to go over, the end of quarter sales reports as well as starting planning for this year’s holiday launch. That was months away as it was only the end of June, but planning always started early to allow for as many ideas as possible. Then there was the whole matter of his recent attitude change and how it was effecting the office atmosphere. 

And of course, there was Castiel. 

_Cas_ as Charlie had called him.

After yesterday morning’s incident, and the conversation later that afternoon, Dean had let his stern CEO façade fall away a little bit. He couldn't deny this nerdy new guy was easy on the eyes, he had this voice that Dean could feel rumbling through every nerve in his body, and he couldn't get the image of piercingly blue irises against flushed cheeks out of him head.

Or maybe Dean just really needed a good, quick bang with the first person he could find.

He couldn't afford to let some stupid little crush get in the way of his business, not again, and so he had avoided the usual end of week drinks the night before. 

With a grumble he hauled himself off the couch and headed to the fridge for another beer, trying to determine whose face he wanted to mindlessly watch for the next couple hours. He was leaning towards anyone with blue eyes.


	11. Chapter 11

Weekends in a new town were always hard for Cas. Give him a couple weeks and he was bound to have a few friendly faces and a handful of plans, but for now he was content with relaxing by himself. Especially considering the headache he had woken up with this morning. 

He had big plans to go for a run, settling himself into a routine while simultaneously scoping out his new neighborhood, but whatever had been in those multiple helpings of _Mojo_ the night before had done him dirty. Cas wasn't all that upset about it; the clouds had finally broken into a persistent drizzle, all but forcing him to curl up on the couch with a cup of coffee and a book. After he'd had plenty of water and some Advil, of course.  
The night was still a little blurry, but he remembers Balthazar beside him in a backseat, and standing staring at his apartment door for what seems like an abnormal amount of time. He felt in his gut that something semi-important had happened, but with the dull throbbing in his head, he wasn't going to dig right now. It would come back to him.

He had mostly finished unpacking into this new little studio, not that he traveled with much anyway. Cas was grateful to be in a city with such excellent public transportation and also to be living kind of close to the office, not having to spend money on gas as frequently would be a blessing to his hopefully steady paycheck. His Kia Soul had taken up residence in a little permit only lot around the corner, where Cas was hoping she would stay safe. He was planning to take some weekend trips to drivable vacation spots around the Pacific North West, maybe even up into Canada, after he got himself settled here. He spent a lot of time on the road between jobs, and he loved it, but it was nice to have something bigger than a car to call his own for a little while.

And so that is where Cas found himself this Saturday. Settled on his little loveseat, letting the rain scented breeze blow in through the window, smiling to himself as he looked around the studio. It seemed different from other places he had lived, but not in a bad way.

He had just flipped open his book when his phone went off, a text from Balthazar:  
_"Cassie! Thanks for the fun night out. Not that it's my business to do, but I would like to officially welcome you to the team!  
Unless of course you didn't survive.."_

Cas chuckled, the throbbing in his head fading away as he responded:  
_"I am alive and well, no thanks to you! Glad to hear I passed your test lol"_

He really had enjoyed himself last night. It had , obviously, been a while since he'd gone out drinking. Despite his hangover, he was glad to have spent time getting to know the team outside of the office.

_"With flying colors! I am sorry about the information overload, I turn into People Magazine when I have one too many ;)"_ Balthazar replied.

Cas hesitated, trying to recall their conversation. He remembered Aaron, and talking to Charlie about Sam -oh you should see the man's hair, Balthazar had said- but after that things get a little fuzzy. Vaguely he can picture Balthazar's face, a serious expression eyeing Cas in the booth - or wait, no, not a booth. A backseat. They had taken an Uber together. Hmm.

_"Oh, don't even worry about it. All in good fun."_ Cas shot him back after a minute, tossing his phone into the pillows next to him.

He leaned his head back and closed his eyes. He wasn't one to black out, no matter how much he had been drinking. Eventually the memories would come back to him, but something about this was bothering him.

He let his mind slide slowly through the events of the day before, fast forwarding through his awkward encounter with his boss, and slowing down to appreciate the lighting and giddy feeling of their conversation later in the afternoon, smiling to himself. He got to the point where Aaron was giving him the details of the information leak scandal, and tripped up a little bit.

Squeezing his eyes tighter he recalled that Aaron had disclosed the leak had been a one man job, but their conversation was cut off when Charlie joined their booth. Pieces of conversation started making their way back into his memory, and with a gasp, Cas opened his eyes wide at the ceiling.

_Oh._

As he let this rediscovered information settle in, he also tried to process what this meant for him.

Why had Balthazar been so intent on telling him this? Was he being watched in his new position in a way he hadn't realized? Was he the reason Mr. Winch- uh- Dean, had been acting like a total dick? 

Cas paused. Had he made Dean blush on their lunch break yesterday? And even if he did, why did he care?

There was no way he could deny that Dean Winchester was handsome, and in the afternoon sunlight with a smile on his lips and his green eyes set ablaze, Cas would argue the man was beautiful. Okay, he wouldn't argue it out loud. This was his _boss_ not some random office employee. That could never happen.

Except that it had, according to Balthazar, and the thought of that made Cas's face hot. Except it had apparently been a mistake, and who knows how much of it was a mistake to Dean. 

Cas sighed, shaking his head. He was in no place to be even thinking about relationships, he was new here, and he knew all of like, six people. If he wanted to stay here, which he thought he might, he couldn't go sleeping around the office.

And so he grabbed his book, forcing any and all work related thoughts from his mind, determined to enjoy his Saturday.


	12. Chapter 12

Monday had, as usual, made an unwelcome appearance far too quickly. The weekend had been full of rain and not much else, and the easy laziness had followed Dean into the start of the work week. He had come into his office to find a piping hot cup of dark roast alongside his stack of morning paperwork, but when he had poked his head out the door to thank Cas, he hadn't been at his desk. Dean had made a mental note to say something later, and taken the cup and his paperwork over to the armchair by the window to ease into the week. He wasn't in the mood to dive in just yet.

Letting the caffeine slowly seep into his veins, he gazed mindlessly out the window, thoughts drifting from work, to Sam, to home where he could barely recall getting himself up this morning. He had skipped the gym, having let the rain convince him to stay in bed, which was probably to blame for his groggy morning. He knew he had a lot to do today, including a conference call with Sam before the usual Monday meeting, but he let himself savor his coffee before he made any moves to get up. Dean noted distantly that he was feeling less tense than he had in months, and wondered if it had anything to do with having someone back outside his office door to help him balance his life.

***

After a few hours of answering emails, collecting sales reports, and putting together the weekly action plan, Dean was itching for the phone to ring. He hadn't spoken to his brother since last week, and he was eager to hear more about the coffee farm he had been scoping out. Dean had gone through Sam's report a couple of times, and the place looked promising. They were hoping to settle a deal and have the stuff on the market by the fall.

Dean was fantasizing about marketing and merchandising when his phone finally rang, and he nearly jumped to grab it off the dock.

"Mr. Winchester, Sam is on the line for your scheduled conference call" came Cas's low rumble through the receiver.

"Awesome, and hey, thanks for the coffee this morning. It made this rainy Monday a little more bearable." Dean shot back, hoping his fluctuation between stern CEO and pleasant boss wasn't screwing with the new guy's head.

"Of course, it was no problem. Glad it went smoother this time." Dean could hear the smile in Cas's voice as his spoke. Maybe a friendly relationship wasn't a terrible idea.

Dean chuckled, "Yes, definitely. Thanks Cas."

He swore, for a second, he heard a sharp inhale across the line before Cas spoke again. "Sure, anytime. I'm going to patch Sam through now. Okay." and then a soft buzzing noise as the line searched for a connection.

Dean was so focused on the quiet hitching of Cas's breath that he almost didn't hear Sammy come on the line.

"Hey, jerk!" came Sam's booming voice, startling Dean from his thoughts.

"Hey, bitch. How's Guatemala?"

"Dean, this place is amazing. I mean, I've seen Guatemala before, but this little mountain valley is incredible! The altitude makes the temperature change between night and day kind of severe, and then the cloud cover adds to that, and it makes the soil and the plants here have all these unique characteristics! I feel like every day I find something new. And the coffee, dude, it's awesome." Dean smiled, hearing the enthusiasm in his little brother's voice. The giant nerd.

Neither of them had ever expected to be where they were in life. Dean had known he would probably inherit the company somewhere down the line, but turning it into what it was today was never something he expected. With his father, John, as CEO, the chain shops had been common enough in bigger cities. With Sam and Dean holding the reins now, they had managed to modernize the company, growing it into one of the most sought after business models in the world. Of course, they would never have been able to do it if their dad hadn't taught them everything before he passed. Dean hoped he would be proud of what they had made, and how much they loved it.

"You're such a nerd, you know that?" Dean teased, pushing his sentimentalities back down. "Do you think we'll be able to do some effective business with them?"

"I'm still working on that. They seem open to the idea, but are worried about their supply meeting our demand. I've been trying to explain the limited edition idea, but they're worried it'll stress the coffee trees to death. Apparently that's a real thing." Sam replied, his optimism seeping into his words. "But I will have an answer for you by the end of the week, definitely. So now, Charlie said you found a new assistant?"

Dean groaned. Of course she would tell him. "Oh, yeah. Castiel. He's only been here about a week, but so far so good. Doesn't seem like he's here to screw us over, at least." He forced a smile, hoping Sam would understand he didn't want to conversation to go there.

"Oh okay well that's a good start" Sam chuckled, "Charlie said you guys had already, uh, gotten to know each other." Dean could hear Sam trying not to bust out laughing. He rolled his eyes.

"Yeah it seems nobody mentioned to him I like to strip down in the office on Friday mornings and he walked right in. Good times for the whole office." Dean wasn't going to make this into anything more than it was, shaking the image of bright blue eyes going wide out of his mind. 

Sam laughed again, "Well, I hope he actually does some good worked, not just getting you worked up."

"Oh my god, shut up Sam!" Dean all but yelled, a grin making it's way across his face. "Will you ever grow out of the Pain In My Ass phase?"

"Alright alright, just poking fun. I'll get back to you about the farm before the end of the week, okay?" Dean could still hear the smile in Sam's voice, but he didn't press it.

"Yeah yeah, sounds good. See ya." He scrubbed his hand over his face as he disconnected, wondering why everyone couldn't just mind their damn business.


	13. Chapter 13

This week had progressed rather uneventfully. Cas kept his newfound knowledge to himself for fear of attracting any unwanted attention, and because he wanted Dean to trust him. From what he had gathered about the way things went down, more people had been hurt by the betrayal than the information getting out. This person had been a friend to everyone, but had really been lying the whole time. Cas wasn't like that, he had no reason to be, and so he set out to be friendly, but not intrusive. So far he liked it here, he didn't want to screw anything up.

He thought it had to be working too. Even though Dean wasn't particularly chatty with him, he greeted Cas with a warm smile when they saw each other, and always thanked him for all he did. Although, Cas didn't think anything he was doing was all that difficult. He was just doing what, he hoped, was in his job description. 

Thursday morning came, and Cas left Dean his coffee and morning work as was becoming normal. He was greeted with a smile and a quiet "good morning, sunshine", causing Cas's cheeks to flush, as Dean strolled to his office. Before he shut his door behind him, however, he paused, and Cas turned to see what was wrong. Dean was standing in the doorway, hand idly fondling the door knob while he furrowed his eyebrows in thought. Cas glanced back out to the office floor, and it seemed nobody else had noticed this change of routine. Cas narrowed his eyes and turned back to Dean, who was now turned back around, watching him.

"Can I speak to you in my office?" Cas felt all the color drain from his face at the question, but nodded curtly and followed Dean through the doorway. "Have a seat." Dean said, gesturing to the chairs in front of his desk. Cas had walked past them every day for nearly two weeks, and never before had they seemed so terrifying.

A million thoughts raced through his head as he sat, Dean getting himself organized. What had he done wrong? Dean had seemed relatively friendly literally moments ago. Maybe somebody had said something about him? Or something about Balthazar? Color quickly flooded back into his cheeks at the thought, and he lifted his eyes from his knees to the green ones watching him from across the desk. Dean smiled.

"Listen, man. I know I came in here like a hard ass on you. I don't want you to think it was personal. You have been doing an excellent job, better than I could have hoped for after having the position empty for those few months, and I don't want you to feel inadequate. So, I'm sorry." He maintained his gaze, smile still on his lips as he waited for Cas to react.

Oh. Okay. 

"Well, uh, thank you, Mr. Winchester. I'm glad to hear that. Thank you." Cas cast his eyes down again, breaking the staring contest he hadn't realized they were having, a small smile tugging at his lips.

"Can I take you out to lunch?" Cas's eyes snapped up again, wide as he saw Dean mindlessly straightening papers on his desk rather than looking at him. "As a like, welcome to the team kinda thing. Obviously. Since you're new. I guess that's obvious too." Dean's cheeks were flushing almost as quickly as Cas's.

Clearing his throat, Cas took a breath, "Yes, sure, that would be excellent. I could use an expert to show me what Seattle has to offer."

Dean seemed to relax at that, letting his eyes meet Cas's again. Cas refused to acknowledge the tiny rumble of butterflies in his stomach. "Awesome," Dean grinned, "If you had nothing planned for your lunch today, there's some good spots not far. I could ask Charlie to join, she thinks you're awesome too. Okay, yeah, I'll just uh pop out there a little later then."

"Sounds good" Cas replied, standing to take his leave. As he reached the door, Dean called to him again.

"And hey, thanks for the coffee Cas."

***

 

His whole life, people had called him Cas. Easier to pronounce and spell than his full name, it had just become who he was. But there was something different about the way Dean said it that made his breath catch in his throat. Even if he would play the sound over in his head, he didn't want to think much more into it. He barely knew the guy.

Charlie had shot him a text shortly after his little meeting with his boss that simply said "LUNCH" followed by several food related emojis. He hadn't seen much of her since the bar last week, so he was excited (and relieved) that she would be joining them. Outside of work, Cas's people skills were a little rusty. Spending much of his time alone when he wasn't at work, despite the friends he had made over the last few years, left him lacking in the small talk department. A couple drinks in him, as evidenced by the previous outing, and he was slightly less awkward. However, there would be no drinks this time.

Just Cas, and Charlie, and their devastatingly handsome boss that Cas was definitely not developing a tiny crush on. Man, once the guy dropped the dick attitude, he was just a normal, likeable guy.

So when Dean came out of his office around 12:30, Cas was trying to convince himself this was just like a business meeting and less like a casual lunch outing. They stood shoulder to shoulder in the elevator, both fidgeting in the silence. 

Dean cleared his throat, "I hope you're not one of those vegans. I didn't account for much other than carnivore when I picked this place."

Cas chuckled, "No, I'm not a vegan. Or a vegetarian. I have quite a broad palate actually, kind of have to when you're in new places so frequently."

Dean turned to him then, arching an eyebrow. "Do you travel a lot?"

"Uh, I guess you could say that." Cas shifted his weight back and forth between feet, looking down, "Did Charlie not mention that part of my resume?"

At that, the elevator doors opened, as Charlie came skidding around the corner. "Guys! Hey!" They stepped out as she continued, "Guys, I'm sorry, I got dragged into something kind of important and I want to see it finished before I take lunch. I was just coming up to tell you." She jutted out her bottom lip, pulling a flawless puppy dog eyed pout. 

Dean let out a dramatic groan, "What _ever_ , dude. More for us then!" Cas couldn't help but smile at the playful attitude of their relationship. 

She swatted Dean's arm as she walked them toward the lobby, "Well have fun, I'll be sure to be at the next one. Or better yet, you should come out to happy hour this week, Mr. Winchester." She let his name roll off her tongue as she winked at them both, then hurried back toward her office. 

"Well," Dean exhaled, "Just you and me, then. Hope you like wings!"


	14. Chapter 14

Dean had proposed having lunch with Cas as a way to kind of face his fears and get to know the guy. It was the least he could do after he'd so easily slid into life here at Winchester Roasters, even after Dean had treated him like crap. He had invited Charlie to alleviate some of the conversation so Dean didn't have to do all the talking. He was usually pretty good with conversation, making small talk, being his usual charming self. But there was something about the way Cas's gaze held such intensity, it made his face warm and his mind go blank. One on one at some tiny booth? There was no way that could be avoided.

Dean had picked a local place, Phoenix Wings, for their lunch spot. Their hot sauces were to die for, and sometimes getting a little dirty over a bucket of wings was the perfect way to relieve some tension. At least, while he was still at work.

They had chatted briefly on the walk over, Dean pointing things out to Cas along the way, including the nearest Winchester Roasters café to the office and apparently, Cas's apartment. It happened to be the one Dean frequented on the weekends, or times when he needed to get work done outside of the office environment. He'd spent many hours there when sitting at his desk proved to be a little too painful to get any work done.

Dean had ordered the classic wings with a side of their famous Phoenix Ash hot sauce, which he made Cas promise to try, while Cas ordered some parmesan chili garlic wings for himself. From there, Dean was surprised, they fell into easy conversation. Dean brought the topic back to Cas's history of travel, which sent Cas on a storytelling spree of his adventures. It was easy to see the guy was passionate about being able to have his freedom, and Dean couldn't help but smile at the way he spoke about each new place with such detail. He reminded him a bit of Sam. Distantly, he noted he would love for them to meet.

It was easy to keep the conversation flowing, as Dean had so much he wanted to ask Cas. Each new adventure sparked new questions, and luckily for Dean, their meal held off Cas's intense gaze for most of the conversation. He was actually having a good time, but didn't want to think too much into that being a good or bad thing.

"So," Dean began between bites, "Why do you stick with this whole secretary gig instead of doing something more travel oriented?"

Cas hesitated as if he didn't really know the answer himself, chewing thoughtfully. "I guess, because it has a relatively steady paycheck, and it's easy to find a position to fill. Even now, this personal assistant thing, it's not technically anything I have experience in, but it worked out."

"Well, I'm glad it did." Dean said, before he could stop himself. Cas looked up at him then, another wing halfway to his mouth, and there it was, his eyes locked with Dean's. 

Oh. Dean swallowed, unsure how to save himself but not able to break eye contact.

"I'm glad too." Cas said after a moment, a small smile tugging at the corner of his mouth. "I'm still getting used to Seattle, but I feel like I could see myself here more long term. It's not quite New York, but in a good way. Like there's always something happening here, but it's not as urgent as other cities." He shrugged then, looking back down at his wings. "Either that or the lack of sun is getting to my head."

Laughing, Dean let out the breath he wasn't aware he had been holding. "Yeah, that happens. But hey just a few hours drive south and you've got sunny beaches in Oregon and California! Weekend trips are pretty common around here, helps clear the cloud cover from your mind."

Cas smiled, finishing off his last wing. "I'll have to plan one of those soon. Or maybe I'll plan to head there next."

"You're going to leave?" Dean said, not quite able to hide the disappointment from his voice. Based on Cas's history, he stayed in on place for anywhere from six months to a little more than a year. He was aware he barely knew the guy, but why bother trying to establish a trusting friendship if he was just going to up and go?

Cas's eyes narrowed briefly, detecting the note of sadness. "Well, I think that all the while I have been traveling to find a place that best suits me. I'd like to find a place that means a little more than just a secretary job, but that hasn't happened yet. But I can assure you, Mr. Winchester, I have no intentions of leaving any time soon. I take my job seriously, and I want to do everything I can to help make yours easier."

He held Cas's gaze with a little more confidence this time, ignoring the fit of electricity flitting through his veins at the sound of his name coming from Cas's mouth like a deep rumble of thunder. He was glad to hear this guy took this seriously, because that was the kind of loyalty Dean needed in someone so close to him. This little lunch outing had helped convince him of that, while also helping to familiarize himself with Cas. He wondered when they would have this opportunity again.

Neither of them spoke, and somehow Cas's gaze softened, but intensified. Dean was mesmerized. His eyes were the deepest blue, flickering different shades in light and shadow. Dean absentmindedly licked his lips, and felt his heart stutter when blue eyes flicked down to watch the small action. 

Dean couldn't deny that this nerdy guy was more interesting than he had originally thought. Dean wouldn't tell him that he thought his lifestyle of travel was incredible, that maybe he could show him more of Seattle, or even the west coast, if he'd let him. Right now, he was trapped in a stare that might as well be seeing straight into his soul, and he didn't mind one bit.

His thoughts, and consequently their staring contest, were interrupted by the waitress clearing her throat, eyes darting back and forth between them. She smiled coyly, sliding the check onto the table before snagging their empty dishes with a wink. Cas ducked his head, but Dean saw his cheeks turn the same color pink as his own as he threw down the company credit card and tried to look literally anywhere else.


	15. Chapter 15

Balthazar, draped over the front desk chatting with Donna, had shot Cas a deviously curious look when he and Dean strolled back into the office together. After thanking Dean for lunch, he collapsed into his desk chair and took a couple minutes to compose himself. He winced when he felt his phone go off in his pocket, knowing exactly what it would be.

_"Out for a little lunch date with the boss, hmm?"_ Balthazar would, of course, want to know all about it.

_"It wasn't a date. He wanted to apologize for being an ass last week and welcome me to the team."_ Cas shot back, still a little tense from the obvious whatever that had happened at the restaurant.

_"Please do tell, as I was never awarded a welcome lunch."_ Cas rolled his eyes.

_"There's nothing to tell, we had some wings and made small talk."_ He hesitated, not wanting to read further into this then he should, but his stomach still being in knots said otherwise. _"Well. Does he have particularly intense and wordless staring contests with all of his employees?"_ He typed, letting out a slow breath and putting his phone face down on his desk to avoid what he knew would be the answer. That had been something, it was almost tangible in the space between them. For heaven's sake, the waitress had even noticed. 

***

 

By the time 5pm rolled around, Cas was itching to get out of the office. He was probably over thinking, but it felt like he was getting more glances in his direction than usual. He wondered just how secret Dean's past relationship had been if this was the way people were reacting to them simply going out to lunch. The weather had turned into something slightly more pleasant, and Cas was hoping to clear his head with a run before more clouds rolled in.

Having been so hyper focused on work since lunch, he had gotten done earlier than usual, and figured he would see if he could leave the couple minutes early. Cas had emailed Dean over a copy of his schedule for tomorrow and an overview of the next week, sent him a reminder to follow up with Sam before the weekend came, and set up the paperwork he would need to look over in the morning. He packed up his things and, with a deep breath, went and knocked on the office door.

A second passed before Dean opened it, looking a little disheveled but smiling when he saw it was Cas. He stepped aside to let Cas in, closing the door behind him. This was the second time they'd been together behind that closed door today, and the thought made Cas's face grow warm. Dean leaned back against his desk, shirt sleeves rolled to his elbows as he watched Cas, expectantly. 

"Um, hello. I, uh, just wanted to see if there was anything else I could do for you before I headed home." Most days, Cas kind of just waited until everyone else started clearing out to take his own leave, but since he and Dean were on better terms he figured some communication couldn't hurt.

Dean watched him still, and Cas began to think this had been a mistake, when he cleared his throat. "Yeah man, you're good. Don't forget to skip on the coffee tomorrow." he beamed, poking fun that made Cas blush a little more. 

"Right, yes, sorry about that again. Uh, well, I'll see you tomorrow." He all but tripped turning around and walking to the door. There was something about being in such close proximity to this man that made Cas nervous. If their conversation over lunch had shown him anything, Dean was just a regular, albeit handsome, guy. Maybe it was the suit, or the private office setting, but Cas felt like he needed to just go.

He was just stepping out the door when he felt a hand on his arm and froze. He turned to Dean, who was standing just behind him, making the hair on the back of his neck tingle. Dean seemed to be particularly focused on Cas's eyes as he spoke.

"I had a good time at lunch today, Cas. Thanks for giving me the chance to prove I'm not always an asshole." Cas let out a soft, quick exhale, and Dean smiled, making Cas all too sure that the man was aware of how he said Cas's name, and he liked Cas's reaction. For a fraction of a second, Cas glanced at the smirking lips, then back up to meet Dean's eyes. 

Was Dean teasing him? What was this? 

"Thanks. Me too." He all but choked out, throwing his backpack over his shoulder and turning to hurry toward the elevators. 

***

 

Going on a quick run helped a little bit, but mostly made him think more. 

Post shower, he heated up some leftover pizza, opting to eat curled up on the couch than like a civilized person at his little kitchen table. He was thinking about all the places he'd been in the past, and more specifically, all the people he'd been with in the past. 

Cas had never really been a relationship kind of guy. His traveling life style kind of prevented it. When he lived in places for longer periods of time, he had occasionally had more serious partners, but he always knew he would be moving on and he didn't want to hurt anyone by ending things suddenly. His last more serious partner, Michael, had been nearly two years ago. Since then, he'd been with a guy here and there, but it had been quite some time. With Dean acting the way he was today, Cas was starting to realize that maybe it bad been too long.

And then there had been his conversation with Balthazar. Of course, Cas knew the weird eye contact thing wasn't just a weird happenstance. Then, he had mentioned the tension in the office, the way Dean smirked when he said Cas's name, they way he had to know he was toying with him, and that he kind of liked it.

Balthazar insisted that he come out to happy hour tomorrow night, and he would pull every string to get Dean to come. He was eager to see what would happen outside of the office setting, despite Cas's protests. He wouldn't tell Balthazar the thought of going out for drinks with the man made his heart race. Not that he needed alcohol to make anything happen, but it would certainly help calm his nerves. He thought briefly how he'd like to return the favor and tease Dean himself, not to mention he was confident he could do a much better job. But maybe not at a work outing.

Cas went to bed with his head in a place it definitely shouldn't have been, both eager and nervous about making it through the next day.


	16. Chapter 16

Dean was pleasantly surprised when he woke to the sun breaking through the clouds. It was nice to go on a run that didn't include a random rain shower, and so he arrived at the office in good spirits. 

After a quick rinse, he exchanged running clothes for business attire, and made his way out to the floor brewing station. As he fixed himself a cup of coffee, a cheerful voice called to him. "Hello boss!" Dean turned to see Balthazar striding toward him, his face split by its usual grin.

"Mornin," Dean smiled, "Ready for the weekend? Hopefully this sunshine will hold out!"

"Oh, yes. It's nice to be reminded what being warm and dry feels like." Balthazar laughed, pouring his own cup. "But the weekend doesn't start till the office gets to happy hour! Will you be joining us tonight?" He asked casually, raising an eyebrow.

Dean paused. The only reason he hadn't made an appearance last week was to avoid all the inevitable questions about his new assistant, but now that they had cleared the air, he thought it might be fun. Maybe Cas would even go. 

"I'm not sure, maybe. Depends how the day goes." He shrugged, he would make up his mind later. 

That seemed to satisfy Balthazar for now, and they walked back toward the main floor where desks and chairs were filling up as everyone started getting to work. There was light chatter humming throughout the room, everyone seeming to be in good spirits due to the nice weather. As Dean planned the room, Balthazar booked behind him.

"Cassie! Happy Friday you handsome devil." Dean turned, following his gaze to where Cas was making his way to his desk. Cas was wearing an ink blue button down shirt, and when he turned to look in their direction, the color made his eyes flash impossibly deeper blue. Dean let out a low breath as Cas started toward them, his shirt sleeves rolled to his elbows, hands stuffed effortlessly in his pockets. Dean wasn't sure if it was the color of the shirt, the combination of black slacks and the brown dress shoes, or maybe that usually his figure was shrouded by some cardigan, but Dean was definitely staring. 

Cas grinned at them both. "Good morning gentlemen." He said, almost playfully. "Enjoying this sunny day so far?"

"Of course, all the sweeter as the week is coming to an end. You'll be coming out for drinks later, yeah?" Balthazar replied as Dean continued to stand there, trying to control his thoughts. 

"Definitely" Cas said, glancing at Dean. "How was your run this morning, Mr. Winchester?"

Dean cleared his throat, rubbing the back of his neck. "Nice. Good. Warmer than usual." He glanced to Balthazar, who was sipping his coffee with a smirk, eyes flitting between the two of them. 

"Well," Balthazar said, "I'll be seeing you later then," and he turned, still smirking, heading back to the elevators, leaving Dean all but sputtering next to his assistant. Cas was watching him with a smile, seeming to enjoy the way Dean's face was growing a shade of soft pink. He squirmed a little under the gaze, and wondered if this was what Cas had been feeling when he all but corned him yesterday afternoon.

"I have to call Sam" Dean blurted out, turning to hurry to his office, ignoring what sounded like a chuckle coming from Cas. He closed the door and leaned up against it, taking a deep breath. This was not happening.

The staring contest incident at lunch the day before had been… something. Dean had gotten lost in his head, and those eyes, and wanted to know more about the man they belonged to. He had spent the entire second half of his day yesterday distracted, and he knew he just needed someone quick to sleep with to ease the tension, but at the same time, he didn't want it gone. There was something almost electric between them; the waitress had seen it yesterday, and it seemed that Balthazar was catching on, too. Was it something to pursue, or something to put an end to?

Cas had to feel it too. There was no way any of that, at the restaurant or in his office, had been an accident. The way he _knew_ Cas's breath caught when he said his name, the way his face flushed when he had gotten close to him. The way he only held Dean's gaze when he thought nobody else was watching. Dean's face was getting warm just thinking about it, thinking about being frozen under Cas's stare while his voice rumbled out-

Nope. This wasn't happening. He hurried to the bathroom, splashing some cold water on his face, jolting him back to the real world where thinking these thoughts about his employees was something he, just a week ago, had vowed never to do again.

Benny hadn't been like this though. Benny had been all too quick, not deep enough, just rough and fun, and comfortable. They had spent little time getting to know each other, and instead spent most of it just around each other. Dean, admittedly, had begun falling for the man for his charming personality. It wasn't until after everything that happened had he realized he didn't know the guy at all. There had been a spark and a flame, but all fires fizzled out eventually. Cas was electric, buzzing with more frequency under Dean's skin every day since the day he stepped into this office.

He took a deep breath and shook his head. Letting the tingle in his nerves settle as he focused on getting his work started for the day, he dialed Sam's number and set his mind to work.


	17. Chapter 17

Balthazar had all but dressed Cas to make this day play out the way he had planned. If this morning's interaction had been any indication, so far things were going perfectly.

Balthazar had texted Cas immediately upon getting in the elevator, sending simply a heart eyes and drooling emoji. Cas had rolled his eyes. Over lunch, Balthazar had spoken enthusiastically about the entire 2 minute interaction, picking apart every detail. 

"You two really do have some natural chemistry, or something. You were right when you said it was almost tangible. The man would be an idiot to not see it too!" He had said between bites of his sandwich. Cas listened with a small smile. He had never been particularly charming outside of the work setting, but with some coaching from Balthazar he had flawlessly executed a 'casual cool interaction,' as Balthazar called it. He was feeling confident, and eager to see how happy hour would go if Dean did show up.

However, as they headed to the bar, his confidence faltered. Like last week, Dean had waved to them as they were leaving, seemingly busy with some paperwork Cas had not given him. Cas worried that maybe his little display earlier in the day had scared him off, more of the playful from a distance type than Cas and Balthazar had realized. Balthazar had ordered Cas a hard cider, not wanting a repeat of what happened last week, and before they knew it they had settled into lazy conversation. Aaron made an appearance again, waving them over to chat with him and Gabriel. Cas noted that he hadn't seen Charlie yet.

Cas was beginning to feel the lazy smile that came before his buzz started to hit, and noted that he probably should have eaten a little more at lunch. As he returned to the table with his second drink, he heard a round of hoots coming from behind him, and turned to see Dean and Charlie strolling into the bar. Cas watched as Dean's eyes scanned the room before locking onto to his own, apparently finding what they had been searching for. He felt Balthazar squeeze his arm, having seen it too, and he smiled, shifting his gaze to Charlie. She waved before dragging Dean to the bar, giving Cas the opportunity to consult Balthazar on what to do next.

"Let him get a drink in first, he has to loosen up a bit. But that looked to me like he knew what he wants." Balthazar made a quick glance to the bar, then reached up to tousle Cas's hair, and quickly undo the top buttons on his shirt. Gabe snickered across the booth, rolling his eyes as he took a swig of his drink. "You two are absurd," he chuckled.

Dean accompanied Charlie on her round of mingling, receiving many excited greetings. Apparently, all of the employees adored him. Gabe mentioned that everyone had been a little put off by his few days of 'dicky behavior,' but they were glad he was back to his social and charming self. Nobody commented on how Cas had been the cause of the negative attitude shift, and he was grateful.

As the pair finally made their way to the last table, Dean leaned to Charlie and gestured toward the bar. He gave them a brief wave as he walked by to get himself another drink. Cas, confidence regained with the help of his table full of wingmen and his slight buzz, downed the last of his drink while watching his boss's ass make its way to the bar. Charlie chatted with them for a second, then turned to Cas.

"You better make a move before he decides to bolt," she said bluntly, and Cas's eyes widened in shock.

"What- how, who else knows about this?" He asked, nerves rising.

"Dude, seriously? You guys haven't been able to keep your eyes off each other since _yesterday._ Trust me. Just go say something. I need to sign on you getting fired anyway if things go south, so don't worry about." She winked at him, stepping aside to let him out of the booth. 

As he got up, Balthazar caught his arm, "Please don't call him Mr. Winchester." That earned a few chuckles from the rest of the table, and Cas narrowed his eyes at them before turning toward the bar.

He stepped up beside the man, raising his empty bottle to the bartender to signal for another, and Dean turned to him. "Hey man, I see Balthazar managed to drag you to another night out, huh?" 

Cas smiled, making sure to catch Dean's eyes as he spoke. "Hello, Dean." He paused, watching the way Dean's eyes blinked wider for a split second, his lips parting with a small exhalation of breath. "Balthazar doesn't have to drag me, I found it quite fun last time. I enjoy getting to know my coworkers. I'm glad you could make it this time."

"Yeah," was all Dean managed to breathe out. Cas smirked, breaking eye contact to take his new drink and thank the bartender. He was satisfied with Dean's reaction, and eager to see what else he could get away with. 

He turned back to Dean, taking a swig of his cider, and giving the man a quick glance up and down. Dean was wearing the same thing he had been wearing all day, almost every day actually. A crisp white button down with some navy blue slacks and brown dress shoes, his suit jacket probably left at the office. Like Cas, his sleeves were rolled to his elbows, top button undone to make himself look at little more casual. In the low light of the bar, his candy apple green eyes had a yellow flare, almost hidden behind pupils blown wide as he watching Cas blatantly check him out. 

Dean took the rest of his whiskey like a shot.

"I think that, in leu of our lunch yesterday, I should buy you a drink," Cas mused with a sly smile, cocking his head to the side suggestively. Dean almost choked. Cas definitely owed Balthazar, big time. 

"Yeah, okay definitely." Dean managed a small smile, then turned to grab the bartender, ordering another whiskey. Cas watched him as he took a sip, closing his eyes as the burn slid down his throat. When he opened them again, his expression had changed. A confident grin tugged at his lips as he eyed Cas with the same intensity he had been given. Cas was suddenly very interested in this little game they were playing. Dean arched an eyebrow at him, "You know, the last time someone looked at me like that, I got laid." He sipped again, smug smile on his face.

Cas raised an eyebrow back, "I hope she had the decency to take you home first, it's seems awfully uncomfortable a thing to do in front of your employees." Cas was careful to mention a female, as Balthazar had warned him however blatant his flirting might be, Dean's bisexuality was still kind of a secret. 

At that, Dean glanced behind them towards the booths of Winchester Roasters employees, as if he forgot they were there. This had been Cas's intention, to distract him enough that he might forget where he was. While the idea of taking Dean home was, at this point, something Cas was definitely interested in, he was having a perfectly fun time with their banter. He glanced back at his table, where Charlie had taken his seat and was deep in conversation with the guys. "It seems Charlie took the last seat, huh," he mentioned, hoping Dean would take the bait to continue their one on one time.

"I think you've got a pretty good seat right now," Dean mused, finally returning the once over Cas had given him. Cas waited to meet his eyes, intending to hold them they way they had at lunch the day before. This time, Cas licked his lips, savoring the way Dean's cheeks flushed pink as his eyes shifted down to watch. His eyes came back up to Cas's, this time with the slightest glint of _hunger_. Perfect.

"I could think of a better one," he smirked, giving himself just enough time to watch Dean's eyes grow wide and cheeks turns dark red, before he pushed back from the bar and walked back to the table.


	18. Chapter 18

Dean couldn't breathe. Was this guy for real? Jesus Christ. 

The guy knew how to play the game, _Dean's game_ , and Dean wasn't used to having it served right back to him. But wow, he kind of liked it. He gaped at Cas, eyes pausing on his ass for a second, as he walked back to where Charlie and the guys were sitting. Balthazar and Charlie both shot Dean a quick glance as they turned to see Cas walking over, probably trying to figure out what had just happened.

Dean slowly gathered himself, downing the rest of his whiskey while deciding his next move. Cas had left the ball in his court, so he could leave, or keep playing. He definitely wanted to keep playing. He grabbed another drink, switching to beer, and wandered back to the table. Cas was leaning against the booth next to Charlie, leaving space for Dean to do the same opposite them, next to Gabe. 

Cas's rumbling voice reached his ears, and the confidence he had faltered. He was afraid to meet the guys eyes, afraid he would devour him right here in front of his whole office staff. So instead, he cleared his throat to signal his arrival and raised his beer at everyone to say hello. 

The conversation was light, full of weekend and summer plans, funny stories from the work week. A couple of things got a soft laugh from Cas, and Dean had paused to enjoy the sound, and the way his impossibly blue eyes crinkled at the corners. More than once, Cas had caught him staring, or been blatantly staring himself, and their eyes met with a raised brow from Cas.

Convinced his cheeks were red enough to attract attention, he excused himself for fresh air. He rounded the corner outside, making sure to get out of sight range before exhaling and scrubbing his hand over his face. What was he doing? This was exactly the thing he had been trying to avoid. And with the first damn guy to come into his life after Benny? He was being an idiot.

On the walk to the bar, he had expressed his concerns to Charlie. At first, she had been giddy with the prospect of Dean getting into a new relationship, and, after calming down, had given him her full support. _Only you know what and when is right for you,_ she had said, _so if you feel something going on here, don't let fear hold you back._

He took another deep breath, rolling his head back against the brick to gaze up at the sky. Seattle had blessed them with a rare day of sun, and even more rare, a clear night sky. Dean wasn't the 'cosmic signs' type, but it seemed like the universe was shouting positivity in his direction since his lunch with Cas yesterday. This didn't have to be a heart break experience like the last one had been, it could just be fun, maybe a friends with benefits kind of thing. Arousal seeped into his thoughts about having a friend with benefits in the office with him, and he smiled to himself. 

Fun. Just for fun. That was something he could do. Something that he probably needed, if he was being honest.

Convinced he could handle this, he took another deep breath and headed back inside. Returning Cas's surprised expression with a suggestive smirk, he jumped right back into the conversation. This time, he made it his goal to make Cas blush with just a look, and so far he was succeeding. More than once, they locked eyes, the conversation continuing around them as their staring contest seeped tension into the air. Eventually, Cas excused himself to go to the bathroom.

Dean didn't mean to stare after him as he walked away, and when he turned back to the table all eyes were on him. He opened his mouth to speak when Balthazar cut him off. "Oh, spare us. Go after him." Dean gaped, but a reassuring smile from Charlie reminded him to fuck what everyone else thought and do what he wanted. _Dean fucking Winchester._

He all but sprinted into the men's room, eyes sweeping for Cas before he was even fully through the door. Cas was at the sink, and spotted Dean in the mirror at the same moment Dean saw him. He eyes went wide at the wild expression on Dean's face, and he turned, speaking his name as a question as Dean closed the distance between them. 

Blue eyes blurred in his vision, closing as Dean's hands found their way into Cas's hair and crashed their lips together. Cas let out a soft moan, wrapping his arms around Dean and pushing, backing Dean up against the wall, the air of tension between them exploding like fireworks the second their lips touched. For a moment they fought each other for control, hands gripping at hair, shirts, the occasional ass cheek, as they spun, pushing each other up against any solid surface they could find. Eventually Cas gained control, dipping his tongue into Dean's mouth, eliciting a noise Dean would never admit to making, and tangling his hands as best he could in Dean's hair. Dean happily gave in then, glad to be taken and had in a way he so desperately needed more of. Cas had his leg wedged between Dean's, their bodies pressed close together against the bathroom wall, feeling every movement of firm muscle, every twitch of pleasure. 

Finally they broke apart, gasping and holding each other. Cas's cheeks were deliciously flushed, his eyes glowing against the bright pink. 

"Dean," Cas all but growled, and Dean let out a soft moan.

"God I love the way that sounds," he laughed, his own voice coming out raspy, still clutching the collar of Cas's shirt. He noted it had become slightly untucked, and wondered if he also looked so disheveled. Cas pulled back far enough to meet his eyes, searching them for where Dean might want to go from here. Before he could say anything, the door swung open, and they jumped apart, turning to the sinks to tidy themselves up while Dean silently prayed it wasn't someone from work. Luckily, the stranger only hesitated a moment, narrowing his eyes at them before carrying on. 

Cas was smiling, watching Dean's face of mild panic in the mirror. Dean straightened, clearing his throat and raising an eyebrow. "Come on, we've probably been gone suspisciously long."

They strolled back to the table, trying to look as nonchalant as possible, despite the small smile tugging at their lips. Dean was glad their friends paid them the courtesy of not making a huge deal as they walked up. The group was getting ready to head out, and Balthazar offered to split an Uber with Cas.

"I think I'd actually like to walk. It's not so far," he replied, and Balthazar grinned.

"I'm sure you could use the time to cool off," he teased, eyes flicking to Dean and back as he followed the rest of the group out the door. "I'll be looking forward to your text!" He yelled back to Cas, and stepped outside.

Dean turned back to Cas, who was rubbing the back of his neck and looking down, trying to hide his reddening cheeks. Left alone, neither of them was sure what to say. Dean knew he wanted to continue this, but he wasn't sure if that would be too much. He would let Cas choose.

"Hey, mind if I walk with you?" Dean asked. They could figure it out on the way.


	19. Chapter 19

Cas was now one hundred percent positive this _thing_ between him and Dean was mutual. The way Dean had looked at him, hungry and desperate, it made sparks fly under his skin. He knew what he wanted, and potentially what Dean wanted, but this was a little more than some random weekend hookup. He had to keep reminding himself this was his boss.

The first few minutes of the walk were filled with an apprehensive air. Cas wanted to get to know Dean more, he didn't want to just bring him home and have his way with him. Well he did, very badly in fact, but he could feel something more going on here. They needed to probably talk about this, but for right now Cas was enjoying the small smirks and glances they were trading as they headed away from the Friday night crowds and into more residential areas.

He took a deep breath, he could do this without totally ruining the mood. Hopefully.

"Dean," he said, glancing over to enjoy the way Dean reacted to him saying his name, "I know the comments I made earlier were not exactly appropriate to say to my boss, and I apologize… I just couldn't help myself."

Dean chuckled, running his hand through his hair before turning to Cas. "You're right, definitely inappropriate, but not unwelcome." He raised his eyebrows in question, trying to figure out where this was going.

"I'm not sure if you'd like to, uh, come in or not. I mean I'd like it if you did, but I wouldn't be upset if you didn't want to. Well, no, I would be upset but I-" Dean's hand closing around his wrist stopped him, and he looked over to meet green eyes.

"I think we could have a lot of fun together," Dean mused, and Cas felt himself growing warm, "I would like to have some fun with you," he paused, giving Cas another once over, "But I also think you're an interesting guy, and I don't want to rush into anything that you aren't ready for."

At this point, Cas wanted to rush. He wanted to fall through the apartment door and barely make it to the bed, not disconnecting their lips even to breathe. He wanted to know what other little noises he could coax out of his boss, and all the ways he could do it. But he wasn't stupid, he recognized Dean projecting a little bit, and was content with knowing this was more than just some one time hookup. And he wanted to find out all that it could be.

He exhaled as they rounded the corner to his apartment, both relieved to be home and disappointed that this was about to end for the evening. 

"That is perfectly fine with me, Dean." He said with a smile, slowing down as they approached his door.

For a split second, Cas saw Dean pout a little, and chuckled. "That walk took far less time than I had hoped," he sighed, following Dean's gaze to his front door. When he turned back, Dean was staring at him, lips parted ever so slightly, as if contemplating his next move. Cas let his eyes slide down to Dean's mouth, nibbling on his own bottom lip for a moment before he let himself give in.

He reached up, slowly, to wrap his hand around the back of Dean's neck, and pulled him in. This time he let their lips slide together slowly, feeling Dean's hands fist into the front of his shirt. He gently nudged Dean's lips apart with his tongue, smiling as Dean let out a soft moan. Cas knew he had to restrain himself or he would be pulling the man in through the door without a second thought. Dean nibbled gently on Cas's lip, taking his turn to follow his teeth with his tongue. They stayed there wrapped up in each other, slowly exploring what they could of each other, before Dean pulled away with a soft gasp.

"Either we stop this for the night, or I won't be able to control myself. Fuck," he ran his free hand through his hair, lust blown eyes never leaving Cas's. "Fuck," he whispered again, biting his lip, breaking eye contact for just a second to glance at Cas's lips, Cas's door, and back to his eyes. 

Cas sighed, knowing exactly how Dean was feeling. "Do you need to call an Uber home? I could invite you inside while you wait…" he said with a smirk, raising an eyebrow suggestively.

Dean chuckled, letting his other hand slowly release Cas's shirt, much to his disappointment. "Weirdly enough, I only live about 4 blocks that way," he pointed over his shoulder, "So I think I'll take Balthazar's advice and walk to cool myself off."

Biting back his suggestion to cool down in the shower, Cas nodded. "Well, please get home safely, then." Cas was still feeling a little bold, the last of his buzz still vibrating under his skin, but he forced himself to hold back. He wanted Dean to feel comfortable with this, despite them obviously both wanting to dive in. He knew Dean needed to build trust after his last relationship, and Cas was willing to be patient.

With a smile, Dean turned to head back down the street, but paused and looked back to Cas. "Goodnight Cas" he said softly, then began his walk home, leaving Cas standing there staring, a flutter in his stomach.


	20. Chapter 20

It was well past midnight, but Dean was wide awake. When he had gotten back to his apartment, he popped open a beer and sat in the dark at his kitchen table, mulling the evenings events over in his head. Going into this, he had planned for something to snap between him and Cas, but he never thought it actually _would happen_. Not to mention the afterwards, it had snapped then exploded in a rain of sparks that were still buzzing around under his skin.

He wanted to call Sam. Or Charlie. Someone, because he was a little lost and a little stunned, and he needed to calm himself down.

He took out his phone, thumbing through his message threads and pausing over Benny's. He wasn't even sure why. Part of him wanted to erase the messages, delete the contact, block the number. Part of him wanted to call him up and scream, he had ruined his ability to trust anyone, to put his all into a person without being afraid. Part of him wanted to see what he was up to, ask him to swing by and relieve some of this tension coursing through him. Instead, he scrolled up to Charlie's messages.

_"Dude, what am I doing?"_ , he typed out, hitting send.

Twirling the bottle in his fingers, Dean thought back to Cas. He thought about the way the other man had so obviously wanted him too, and just as badly. The way his breath caught when Dean said his name, the way he had so gracefully taken control in the bathroom, the way he had been almost soft out there on the sidewalk. He thought about the way he had laughed with all the other employees over drinks, the quality of their conversation at lunch the day before. Dean was struggling to push back what his brain was screaming at him, trying to regain focus on the whole 'just for fun' thing.

He sighed, not sure what the next move to make was. He wanted to get to know the guy more, but he also wanted to keep his distance _romantically_. He couldn't afford what this getting serious, going public, would do to his career. If that meant taking a potential relationship off the table, then so be it.

*** 

 

It had occurred to Dean halfway through the day on Saturday that he, in fact, did not have Cas's number. At first, he had pouted, wondering if it would be too… needy if he asked Charlie for it. Sam had told him to suck it up and contact the guy if he wanted, but Dean knew it would give the wrong impression to Cas.

So when Monday rolled around, he had made up his mind to not make this into more than what it was, fun. Cas gave him a quick glance, accompanied by a deep blush and a smile as he had walked into his office. He wasn't sure if Cas was the kiss and tell type, and so making any obvious advances in the office was out of the question. He did make more frequent trips outside of his private office than he needed to, however. Cas was, once again, wearing a slim fitting button down and slacks that hugged him in all the right places. His hair was a little unruly, but his eyes their usual breathtaking blue. He had caught Dean checking him out at least once, and met Dean's slightly embarrassed gaze with the raising of an eyebrow. After lunch, on Dean's third unnecessary trip to the brewing counter, his thoughts were interrupted by a deliciously rumbling voice behind him.

"Mr. Winchester," Cas greeted him with a smirk, "I would hate for you to be away from your desk any more often than necessary. If you need me to bring you in more coffee I would be glad to do it." 

Dean, trying to play coy, smirked back at him, but faltered when he realized he hadn't thought of what to say when this confrontation eventually occurred. He held Cas's gaze over the rim of his cup, sipping slowly to buy himself some time.

"Thanks, Cas. I'll be sure to let you know when I need a refill." He settled on.

Cas cocked his head to the side and squinted at him then, as if trying to see through Dean's play. He leaned in ever so slightly, and Dean froze, eyes going wide, frantic. Cas's arm reached up slowly and Dean felt like his heart would burst through his chest. They were alone and out of eyeshot of the rest of the floor, but someone could come over at any moment and-

Cas's arm reached behind Dean, grabbing a mug off the counter and stepping to the side to pour himself a cup. Dean let out an audible exhale, narrowing his eyes when he saw Cas's mouth twitch up in a quick smirk.

"Well, Mr. Winchester, don't hesitate to let me know if there is anything, anything at all, I can do for you." Cas said, turning and strolling back to his desk.

It hadn't occurred to Dean that having fun might be a two player game.


	21. Chapter 21

Cas didn't expect to hear from Dean for the rest of the weekend. On Saturday he had woken up feeling content, went on a quick run before the clouds had a chance to roll in, and made plans to spend the say with Balthazar. Balthazar had insisted he continue his services as Cas's coach through his process, and so they did some shopping, some Seattle exploring, and some socializing.

"If there's one thing I've observed of Dean, Cassie, it's that he likes to play like he has everything under control," he had said, "And so I think the most logical way to approach this is to unravel him a little bit. Let him know you can play the game just as well, if not better."

Balthazar knew Cas wasn't exactly a social butterfly, and so they went through a few hours of working flirty body language into Cas's every day vocabulary. Lots of smirking, eye contact - but also let the eyes wander- and push personal space boundaries. 

"And _please_ make use of that sex voice you have," Balthazar had said, and Cas blushed.

"It's just my voice, I don't do it on purpose," he had replied.

Exhausting as the day had been, Cas had gotten to see a lot of his neighborhood, realizing he was a few short blocks from the Winchester Roasters he had walked past with Dean on their way to lunch. 

When Monday came, his nerves were buzzing with both anxiety and excitement. 

Dean had given Cas his usual greeting, and Cas found himself unable to speak as Dean's voice brought back a flood of Friday night memories. He had smiled briefly, then distracted himself in checking Dean's schedule and writing out some emails. That, however, was about the last 'normal' interaction they had for the rest of the day. Cas couldn't ignore the frequency with which Dean was out and about, roaming the office. He was chatting with people at their desks, using the floor bathroom rather than his private one, and making far too many trips to the brewing counter. More than once, Cas caught Dean staring at him, and finally decided to make a move.

He followed Dean around the corner to the brewing counter on what had to be his third trip today, in addition to the coffee Cas had left on his desk this morning. He paused to admire his boss from behind, mindlessly biting his lip as Dean's bow legged stride brought him up to the counter. He took a deep breath.

"Mr. Winchester," he smirked, "I would hate for you to be away from your desk any more often than necessary. If you need me to bring you in more coffee I would be glad to do it." 

He watched as Dean tensed for a moment before turning around, eyeing him over the rim of his mug. Cas made sure to hold his gaze.

"Thanks, Cas. I'll be sure to let you know when I need a refill." He finally responded.

Deciding to play with personal boundaries, Cas made a slow but deliberate grab for a coffee mug sitting on the counter just behind Dean's hip. He let his fingers trail dangerously close as he leaned in to grab it, watching his boss's face flush. With a smirk, he stepped to the side to fill the mug, then returned his gaze to Dean's.

"Well, Mr. Winchester, don't hesitate to let me know if there is anything, anything at all, I can do for you." Cas supplied, maintaining his smug smile all the way back to his desk. He plopped down, sipping at his coffee before starting to make it look like he was doing some important work while he waited for Dean to return to his office. 

After a few moments, Dean appeared around the corner, keeping his eyes down as his made his way to his office. As he approached, he lifted them to catch Cas's, and he looked like he might say something, before changing his mind and continuing through his door. Cas wasn't sure what to expect, as they were still at work and he knew Dean didn't want this to become obvious, but he had a feeling the man wouldn't be able to ignore it for long. The sizzling tension they had been struggling with last week was making it's way back into the air, and Cas couldn't help but feel giddy as it buzzed under his skin. He could wait, if that’s the game Dean wanted to play. 

As the end of the work day approached, Cas felt disappointment settling in his gut. Dean had made no more trips out of his office, and Cas was beginning to worry maybe making any moves at work was where he drew the line. He began slowly packing up his things, eager to leave the moment the clock hit 5, when his desk phone rang. Odd for being so close to closing time.

"Winchester Roasters, desk of Mr. Winchester, how can I help you this afternoon?" He said.

"Cas," Came Dean's voice, "If it's not too much trouble, could you grab me a cup of coffee?" Cas could hear the smile in his voice. 

He hesitated before answering, "Of course. Anything else?"

"Nope, thanks." Dean said, and the call ended.

Cas turned around slowly, narrowing his eyes as the vague shape of a desk behind the frosted glass, before heading over to grab Dean's coffee. With a little smirk to himself, he undid the top button of his shirt. _Just for a little fun._

He knocked, waiting just a second to hear Dean's reply, and walked in.


	22. Chapter 22

Dean needed to release some of this pent up tension or he was going to lose it. He toyed with the idea of relieving himself in his private bathroom, but why would he do that when the source of his frustration was just outside his door?

He eyed Cas hungrily as he walked through the door, making his slow sweep of Cas's lean body as obvious as possible. He loved the way Cas's cheeks flushed pink when he realized what was happening. Cas's lips parted slightly as he placed the mug down on the corner of Dean's desk, then took the extra step that brought him around to the side, Dean smirking up at him. A beat passed before Dean lunged.

He pushed Cas back up against the desk, fisting his hands in the man's shirt in one fluid motion. Cas's eyes widened, flicking to Dean's lips, then back up with meet green.

"You're driving me crazy, man" was all Dean could find before catching Cas's lips in his own. Both of them letting out soft, satisfied moans, Dean felt Cas's free hand find it's way to his hip, digging his fingers in and pulling him closer. Dean's fingers twisting in Cas's dark hair, he let their tongues slip together, then let out a deep moan as Cas's hips twisted up, creating a delicious friction. He pushed back, harder, more deliberate. _Fuck._

With a gasp they broke apart, still clutching each other. Cas's hair was impossibly more wild, his lips red and swollen from the intensity of their kissing, and Dean felt suddenly and hopelessly lost in his need to make Cas look even more disheveled. Cas seemed to understand, and with a smirk he pushed up from the desk, gently walking Dean back to press him against the wall of windows, and find his way to Dean's neck.

_Oh, fuck._

Dean squeezed his eyes shut, savoring the feeling of Cas's light covering of stubble raking across his skin. Cas's lips were gentle at first, kissing and softly sucking their way down below Dean's collar. He started his journey back up to Dean's jaw, nibbling the soft flesh. This time, Dean's hands found their way to Cas's hips, pulling them together tightly.

"Cas," he breathed, unsure of what he was even asking.

Cas continued his exploration of Dean's neck, a smile on his lips, as his hands slid slowly down Dean's chest. Dean's heart began to race, eyes opening to flick towards the door, suddenly all too aware of the vague figures moving around the office outside. He felt a soft tug at his stomach, Cas gently pulling at his shirt to untuck it, but giving Dean the opportunity to stop him if he wanted. 

He didn't know what he wanted. Well, okay, no, he _knew_ , he just wasn't entirely sure it was a good idea. Was this moving too fast? Wasn't that part of the fun? What about all the people who definitely saw Cas walk in here just a few minutes ago?

A slightly too hard nibble at his collar made him refocus, and he made a decision. He pulled Cas's hips hard into his, fitting against him and causing Cas to breathe a downright filthy moan into his neck. He nudged at Cas's cheek, bringing his face up to catch his mouth in a kiss, and forced them back till Cas's bumped Dean's desk. Now, it was Dean's turn to explore, and he continue to push himself into Cas as he mouthed his was along his jaw line and down his neck. He shifted his hips once more, just slightly, to line up their not so subtle boners, and began to grind into Cas.

Cas fell apart. Dean smirked against the man's neck, alternating between nibbling, sucking, and moaning himself, while Cas's hands searched for something to hold onto. He was biting his lip to hold back soft whimpers, and so instead they were coming out as low moans in his throat. They should stop, Dean knew, but this was too good, and he was enthralled in the way he had Cas squirming in his hands.

"De- Dean, I can't, I-," Cas gasped, and Dean slowed himself to a stop, pulling back to look at this artfully disheveled man in front of him. Cas blushed, catching his breath, "I'm sorry, I- it's been a while," he panted, casting his eyes down.

Dean's own cock twitched, wanted release after getting so worked up, but Dean ignored it. "Do you want me to…" he trailed off, raising his eyebrows at Cas. He could take care of himself later if Cas wanted out.

Cas's hands still hadn't let go of Dean's hips, and he bit his lip in thought, glancing from Dean to the office door. With a soft smile, Dean grabbed one of his hands, pulling him up from the desk and leading him across the office to the private bathroom.

He didn't bother closing the door, but instead pulled Cas in and then pressed him up against it. Resuming his grinding, he began to undo the buttons on Cas's shirt, eliciting a quick inhale from the man before he followed suit. Dean kissed him long and slow now, matching the pace at which their bodies moved together, trying to work Cas back up to the wriggling mess he had been just a minute ago. He reached down then, pulling at Cas's belt, undoing his pants and pushing his hand in to wrap around him. Cas let a soft whimper escape from between their lips, his own hands searching for Dean's waist, but Dean swatted him away. He undid his own pants as he continued to stroke Cas slowly, then, pushing himself closer, took both of them into his hand. He grinned as Cas broke their kiss to let out another low moan, his head thudding back against the door.

Dean went for his neck, and now, exposed chest, sucking and biting harder in places Cas's shirt would cover. He stroked them both slowly at first, but as Cas began to crumble again, he sped up. Cas was no longer trying to stifle his noises of pleasure, he hands finding purchase on Dean's hips. Dean could feel himself getting close, and judging by the way Cas was beginning to shake, so was he. He pulled back, giving himself room to watch as Cas fell apart in his hands.

"Dean, fuck," was all the warning he got, Cas's eyes squeezing shut as he threw his head back and let out a long, low, groan. Dean stroked him through it, resting their for heads together just as Dean came undone himself. They stood there for a moment, panting and holding each other up. Dean pulled away with a soft chuckle, a warm blush spreading across him as he took in the sight before him. Leaning back against the door, Cas's hair was sticking in every direction, his blue eyes fluttering open but still striking against his flushed cheeks. Shirt thrown back over his shoulders, there was a peppering of deep red bruises appearing across his exposed chest where Dean had sucked a little too hard, and then what looked like miles of tanned skin stretched taught over the muscles of Cas's abdomen. A splattering of wet spots dotted the skin below his stomach, just above where he was tucking himself back into orange boxer briefs. _Delicious_ was the only word Dean could think.

Dean turned away in search of a towel to clean up with, while simultaneously trying to hide his own reddening cheeks. This guy was damn hot, and Dean wanted to do _that_ again, like soon. Cas smiled softly as he accepted the towel, then eyed Dean from under his dark lashes.

"I apologize for driving you crazy," he said, his voice coming out, if it was even possible, raspier than usual.

"If this is the way we end up, you can drive me crazy any time you want," Dean chuckled.


	23. Chapter 23

They had gotten themselves back together slowly, all glances and soft smiles, both tired from the long day of tension and the exhausting release of it all. Dean had followed Cas out of the office, pausing in the doorway to throw anyone that might be listening off their trail.

"I appreciate your input Cas," he had said, just loud enough that anyone pretending not to listen could hear it, "I'll think it over and I'll get back to you before the end of the week." Dean had caught his eye and winked at him then, before wishing him a safe home.

Cas tried not to appear any level of smug as he made his way out of the building, waving his usual goodbyes to Donna and anyone else he happened by. Naturally, he hadn't quite made it to the front doors before Balthazar's boom stopped him.

"Cassie! Let's walk together, shall we?" He waggled his eyebrows as he approached.

"Hello, Balthazar," he said, not able to hide the smile from his voice. 

Balthazar paused for a moment, interpreting, before his eyes went wide. "Oh why yes I would love to grab a drink with you!" He said, all but dragging Cas out of the building.

Twenty minutes later, they were the only people seated at a high top in some cocktail lounge a few blocks away at 5:30 on a Monday afternoon. Balthazar had, of course, ordered them something eccentric and fruity, and was sipping it with wide eyes as Cas recounted what had happened. A smile gradually spread across his face as Cas's began to blush, hurriedly skipping over the details to the end. Balthazar sat back and clapped his hands together.

"Well, my god, now that you've had it, you need to play hard to get." Cas stared at him, unsure how Balthazar formed these plans in his head. With a roll of his eyes, he continued, "Look, now he's going to be 'asking for a refill' whenever he pleases! You need to exert some control of your own." He stopped, sipping thoughtfully at his drink while Cas waited for his plan to unfold. 

"Oh!" He exclaimed, "You have to see if he can hold out till Friday. Get him when he's coming in from his run." He waggled his eyebrows at this, and now Cas rolled his eyes.

"I can't just walk in on him!" Cas huffed. Why couldn't he just take the guy out for dinner? 

Balthazar's eyes grew wider, "Or, he could walk in on _you._ "

***

 

The week progressed… frustratingly. Cas liked the idea of surprising Dean and dominating the experience, but it was all the _waiting_ that was killing him. Dean continued to make teasing advances, and Cas happily gave them back, but he wanted more. 

On Thursday morning, Dean had been at the office before Cas. When Cas went to leave Dean's morning coffee and paperwork on his desk, the man had all but ambushed him as he came in the door. Coffee falling to the wood floor, Dean had thrust Cas back against the door, and Cas had tried to tangle his fingers in Dean's hair while still clutching a handful of paperwork. When they came up for air, Dean's eyes were wide and ravenous, and Cas had used the excuse of getting a fresh cup of coffee and some paper towels to prevent Dean from devouring him on the spot. It was evident Dean was frustrated, but was definitely not keeping his cool as well as Cas.

Hours later, Dean showed up exasperated at Cas's desk. "Come to lunch with me," he didn’t ask, but his eyes were pleading. How could Cas continue this blatant torture?

They sat across from each other, waiting for their burgers, Cas smiling smugly while Dean eyed him suspiciously.

"Did I do something? Was that too much the other day? I can't stop thinking about you and I don't know why" Dean's words came tumbling out, and Cas felt himself falter.

"Dean, no, you didn't do anything wrong," Cas said slowly, "I just, I don’t know, it's work and you're my boss and…" he paused, trying to figure out where to go with this, "And I wouldn't want people to think any less of you as the head of this company for being involved with someone like me." He knew that would hit home with Dean, and he hoped it would be appreciated even if Dean didn't know that Cas knew the truth.

It worked, apparently, because Dean's face contorted into something a little sad while being simultaneously grateful. He looked around then, scanning the restaurant, then shook his head.

"Listen, Cas. It's nobody's damn business. I love my team, I really do, but they tend to stick their noses into stuff they don’t understand, and they don’t realize who they can hurt…" Dean trailed off, and Cas had to prevent himself from prying. He had the feeling Dean would tell him on his own terms. 

He changed the subject. "Dean, how did you and your brother become involved in all this?" Dean smiled, and launched into his life story, about his parents and his brother and how this company had come to be his. And Sam's, of course. Cas listening intently, mesmerized by the way Dean spoke so fondly of his brother, of their relationship and the work the did together. Cas thought distantly that he would like to meet Sam.

As they waited for the check, Dean looked up at Cas, thoughtful. "So, actually, this afternoon I'm supposed to have a sampling of a new coffee Sam has been researching. Uh, usually, it's just Charlie and I, and Sam if he can make it home, but if you're interested, maybe you can join us?"

Cas stared, excitement bubbling in his chest. He had no dreams of being a bigger part of this company than he already was, but the idea of being a part of a process so crucial and often overlooked, that would be incredible.

"Or, you know," Dean said, quieter, "you don’t have to. It's whatever. Charlie had mentioned you were really passionate about the whole com-" 

"Dean," Cas cut him off, "Yes. Yes, absolutely yes. It would be an honor." Dean smiled, looking away to take care of the bill to hide it. "But Charlie wasn't supposed to tell you what a giant nerd I am," he added, getting a chuckle out of Dean.

Cas noticed the way Dean's eyes got all crinkly at the corner when he laughed.


	24. Chapter 24

He figured maybe jumping into this fire was the easiest way to get over the fear of being burned. Dean wasn't trying to recreate his relationship with Benny, but he needed to get past all the crap he associated with it if he wanted things to move forward with Cas. 

Just the thought made his heart race. Did he want to move things forward with this guy? In the short few weeks they had known each other, and even shorter time they spent getting to _know_ each other, Dean had found himself stirring from thoughts that centered around Cas more often than not. He told himself it was just the thrill of having something new, but at the same time he couldn't shake the feeling of wanting more, of something bubbling under the surface. He liked having Cas's around, and for now that was what he was going to focus on.

When he walked back into his office with Cas in tow, Charlie was already setting up their little tasting. She raised an eyebrow briefly at Dean, who simply smiled, knowing she would want to hear about it all later even if he addressed it now. 

The three sat down in the tasting corner, settling into comfy armchairs surrounding a small coffee table. Charlie had set up a French press with the new blend, accompanied by a plate of chocolate chip muffins and some mugs. Usually Sam was here to guide them through this process, but today they were going to Facetime with him instead. Dean's stomach lurched as he considered that this would be the first time Sam 'met' Cas, and as it currently was with Charlie, bringing Cas here would raise some questions.

Dean glanced to Cas, smiling as he watched wide blue eyes take everything in. When they met Dean's eyes the softened a little, nerves easing for the both of them. Dean was minorly aware of Charlie beaming at them in his peripherals. His phone rang.

"Sammy! Can you hear me?" Dean said, propping the phone up on the table so everyone could see.

"Hey guys!" Came Sam's voice a moment before his face appeared on the screen. 

Dean figured it was best to just jump into this. "Hey so Cas is here with Charlie and me, I asked him to sit in on this tasting, hope that's cool."

Sam's eyes went wide for a moment, but then his face split into a grin. Cas leaned over slightly to make himself visible to Sam, "Hello Sam," he rumbled, and Dean couldn't help but smile.

"Glad to meet you, uh, sort of, Cas! I've heard lots about you!" Sam said with a wink, causing both Cas and Dean to blush, Charlie letting a small giggle slip out before her hand shot to her mouth. "Alright, alright. Let's get this started."

Sam began a long winded explanation of this coffee and what made it so unique. Dean loved how passionate Sam was about these things, and he appreciated all of the work Sam put in, but he liked the _tasting_ part more than the research. What held his attention was how intently Cas was listening in, his brows furrowed ever so slightly, his lips parted as if a question was waiting just on the tip of his tongue. More than once Charlie playfully kicked his foot when he had been staring for too long. He couldn't help it, the guy was kind of adorable, but he would never admit that.

The tasting process was kind of cool. First they smelled the beans, the first ones roasted just for them. Then the grinds, coarsely ground for a French Press, and then finally, the coffee itself. Sam went over the different notes the coffee had, and how they changed slightly through the brewing process. Slurping the coffee, they discussed the flavor profile, how it felt on the tongue, all the boring stuff people don't think about when they're chugging through 3 cups a day. And finally, the pairing. Much like a wine pairing, all coffees pair with foods that help to accentuate their flavors. In this case, the dark cocoa notes paired beautifully with the chocolate chip muffins. This was Dean's favorite part, and he savored the way the paired combined on his taste buds. 

The room was silent for a moment, save for some quiet slurping, as they enjoyed the afternoon snack. It was Cas who finally broke the silence.

"So, if you don't mind me asking, what will you call it?" He asked.

"Well," Sam began, "usually that's on the tasting team as they spend so much time really getting to know each blend. But I think this one is special, and if I have a say I'd like it to have something to do with where the beans are grown. This place really is like a little Eden hidden in the mountains."

"Heavenly," Cas mused, taking another sip.

Dean had barely spoken this whole time, distracted by the way Cas was taking it all so seriously. Charlie had been right to pick him for this company. He was passionate in all the right places, he was eager to learn more and share ideas. He really was such a unique find. Dean smiled to himself, all too aware of the parallel between Cas and this 'heavenly' coffee. _Guess that makes him some kind of angel_ , he mused.

As he had suspected, Cas hit it off with Sam almost immediately. While the nerds talked, Charlie pulled Dean away to his desk.

"So, uh, what's up?" She asked, her voice quiet as her eyes glanced over her shoulder at Cas.

Dean hung his head, bringing a hand up to rub the back of his neck. "Charlie, I don't know. After the other day I just can't get him out of my head." He paused, looking over to where Cas was listening enthusiastically to whatever dorky thing Sam was saying. "It's different. I feel like I can't get enough… like I want to just know everything about him."

She raised her eyebrow slowly, "Are you, like, dating? Or…"

"No, no, we're…" he sighed, "We were just having fun but there's something else there, tugging at my chest. With… _him_ it had started so intensely physical we just kind of fell into each other. But with Cas well, I don't know. I definitely want it to be physical but I think I want more, too. But, what if…" he trailed off, casting his eyes down now. _What if he's using me again,_ was too much to say out loud.

Charlie's hand was on his shoulder. "Hey," she said, catching his eye, "He's different, I can see it too. The way you look at him like you're trying to memorize every detail of him… you like him, dude. Like real people, crush to dating to whatever else happens, you like him." 

Dean could feel his face heating up. "I can't… date him, Charlie." He said, without looking up.

She let out a puff of breath, looking quickly back at Cas before continuing, "Dean Winchester, stop worrying about everyone else and worry about you. What do you want? Why don't you try just opening up to someone, see where that gets you? Try a different approach this time! And please, everyone loves and supports you, and we are willing to take down anyone who says otherwise. Do something to make you happy. Take the man out on a date _without_ the company credit card."

He smirked, mostly annoyed that she knew him as well as she did, but also happy at the thought of being happy. And maybe a little at seeing Cas in casual clothes, too.

They were pulled from their conversation by Cas clearing his throat, walking toward them with Dean's phone showing Sam waving enthusiastically. "I gotta go guys, I'll talk to the guys over here and get more product up there by next week! Love ya'll!" Sam disconnected before anyone could respond.

For a moment they stood in silence, Charlie not entirely done with her pep talk and Dean not done with repressing his feelings. 

"Welp," Charlie said, "This was fun! See you guys later." She gathered up the French press and scurried out of the office, leaving Dean suddenly too warm and all alone with Cas. As the door clicked shut, Cas reached his hand out to touch Dean's arm.

"Dean this was a very unique experience. I hope I didn't intrude, but I did enjoy myself and thank you for inviting me." He smiled up at Dean through his dark lashes.

"I'm uh, glad you came Cas." He swallowed thickly, "I'll be sure to let you know if we do another. Uh. I should get back to work." He instantly felt the cool wash of air as Cas's hand left his arm.

"Of course, Dean. Let me know if you need anything." And he turned and left.

Dean let out a shaky breath. How the hell was he supposed to ask this guy out on a real date?


	25. Chapter 25

Cas was still trying to get himself on board with whatever it was that he and Dean had going. They're conversation over lunch had him leaning toward something with the potential to become more serious, but the way Dean acted afterward, in front of Charlie and Sam, made Cas feel like maybe this was something better kept quiet. Mixed signals aside, Cas was one hundred percent sure he wanted Dean either way.

Friday morning came, and with nerves one fire Cas set out to enact the plan he and Balthazar had cooked up earlier in the week. He had to get to the office early, before anyone else, including Dean, was there. Stowing his backpack out of sight under his desk, he slipped around the corner to where the coffee brewers were. From there, Cas could peek around the corner and ensure Dean made his way to his office after his Friday morning run. He was fidgeting, about to just call it quits from being so anxious, when he heard the ding of the elevator.

Peering around the corner, Cas watched as a rain slicked Dean stepped from the doors and headed toward his office. His breath caught as Dean pulled his shirt off only midway to the doors, jogging the rest of the way. As the door clicked shut, Cas smirked to himself, nerves alight once more as he quietly made his way down the same path Dean had taken. He pressed an ear carefully to the door, making sure he heard nothing for a good minute before taking a deep breath and pushing inside.

Dean's rain soaked clothing littered the floor in a trail to the bathroom door, which was cracked open, steam curling out in wisps. Cas hesitated, wondering if maybe he could get away with hopping in the shower with him, but decided he didn't want security called if that went south. If he was being honest with himself, anything he did right now could go horribly wrong. He was confident Dean was attracted to him, sure, but there was that tug of doubt at the edges of his mind telling him not to try anything, the man was _his boss._

He shook his head, expelling negative thoughts and setting his mind straight. He was here to have fun and see where that got him. With a deep breath, he undid the buttons at the top of his light blue button down (Balthazar said it made his eyes shine like ice in the sun), and ran his fingers through his hair, taking a seat in Dean's desk chair. Eyes glued to the bathroom door, he waited for the shower to turn off.

Cas could hear Dean humming to himself, and couldn't help but smile. Moments later, the door swung open in a puff of steam, revealing a freshly showered Dean wrapped in a towel, skin still pink and glistening from the hot water. Cas's breath caught in his throat, mind going blank for a second.

"Cas!" Dean yelped when he finally caught sight of him, taking a startled step backward.

"Hello, Dean" Cas growled, getting up and crossing the room with cat like speed. He caught Dean's hip in his hand, burying his face in his neck as he slowly walked them back against the wall. Dean gasped as Cas nibbled at his neck, stammering as he tried to gather his thoughts.

"Wha- what're you, oh- Cas, what- " Dean tried, cut off by Cas's lips catching his. Cas could feel that he was a little tense, unsure what was happening, but he wasn't fighting it.

Cas broke the kiss, nuzzling his was along Dean's jaw before finding his earlobe and sucking gently, "I want you, Dean" he whispered.

He felt Dean stiffen is his arms, the man's breath hitching deliciously. Cas smiled, continuing his path down Dean's jaw, pressing himself against the towel separating them.

Then, Dean's hands were at his shoulders, pushing gently. He felt his stomach drop as he stepped back. Dean didn't want this.

Holding him at arms length, Dean searched his face until he caught Cas's eyes. "Hey, whoa, slow down there cowboy." He flashes Cas a reassuring grin. "Can we talk for a sec?"

Cas could feel his cheeks flushing, mortified to have misread this whole situation. Who was he kidding? This man was his boss, a business icon, he didn't want any kind of relationship with his secretary. This had been a mistake, and he should never had let Balthazar or anyone talk him into this. 

He stepped back, turning to make a break for the door, slipping from Dean's hands. 

"Cas, wait-" Dean said, eyebrows furrowed. He launched forward, clutching his towel with one hand and reaching for Cas's hand with the other. Spinning around, Cas's eyes were cast down, cheeks burning hot. He needed to say something. 

"Dean, I can read the signs, you don't need to say it out loud. I know rejection when I see it, please just let me go." He blinked back the hot pricking of tears. He shouldn't care so much.

"Whoa, whoa, whoa. Cas, no. That's not- " He scrubbed his hand over his face, starting again. "I like you, man. I want you, too, believe me. I just… I wanted to uh- would you like to get dinner sometime?"

When Cas looked up, this time Dean's eyes wouldn't meet his. The man's cheeks were blossoming a deep pink as Cas worked out what was happening.

He squinted at Dean, tilting his head to the side, "Are you… asking me out?"

"I uh, yeah. I guess so. Yes." Dean's eyes flitted up to meet his, a small smile tugging at his lips. Cas's mouth twitched up at the corners as well.

"I'm free almost any night of the week." Cas rumbled at him, slowly reaching out to touch Dean's arm. Apparently he couldn't read the signs at all.


	26. Chapter 26

So, Dean had a date. He didn't tell anyone, not Charlie or Sam, not a single person. Let everyone talk as they will, but this was his little slice of joy he wanted to keep to himself. 

He had gone out for drinks with the team Friday afternoon as usual, trying his best not to stare (more like gawk) at Castiel every chance he got. The guy was reverberating confidence, happiness even, his usual furrowed brow replaced with a soft smile for the whole evening. Dean managed to coax him outside to steal a few kisses. Dean wanted more, to take him home, to leave everyone else, but he was going to be patient with this one. 

Dean did offer to walk him home again, though. He was sure he could resist the urge to follow the man inside, spend the night with him. Both of them relaxed after a few drinks, they chatted effortlessly the whole way. It felt good, right almost. Slowing things down suited Dean, he liked the idea of really getting to know someone. Cas.

They parted after a soft, shy kiss in front of Cas's door, a whispered _Goodnight, Dean_ tickling his ear before Cas stepped away. He would be back here tomorrow night to pick Cas up. The rest of the way to his own apartment, Dean smiled to himself.

***

Dean was a little nervous that Cas would be bored. Sure he had mentioned wanting to explore the city, but he'd been here for weeks and maybe what Dean had planned wouldn't be any fun. Maybe Dean was just getting nervous, and maybe he needed to just do the damn thing because he liked Cas and he wanted to hang with the guy.

They had plans for dinner, but Dean had arranged to pick Cas up a little earlier to do some sight seeing before they ate. Dressed in a lightweight flannel over a black t-shirt and dark jeans, his nerves were making him warm on a cool evening as he approached Cas's block. A smile tugged at his lips as he thought about kissing Cas again, his gut telling him this was more than he had thought he could get himself into again. 

It was different to be here in the light of day, and Dean had to double check he was in the right place. He took a deep breath and knocked, rather than just texting the guy. After a moment, Cas jerked the door open, his hair tousled perfectly, eyes wide, then crinkling at the corners as he smiled at Dean. It was contagious, and Dean couldn't help grinning back at him.

"Hey, Cas" he breathed, taking in the man's casual attire. He could get used to _that_. Cas was wearing a powder blue Henley rolled up to his elbows, dark jeans and sneakers.

"Hello, Dean," he responded, his voice the usual rumble with the twinge of a smile on his lips. The two stood in the doorway smiling at each other before Dean cleared his throat, cheeks flushing.

"You ready to go? Up for a little touristy evening?"

Cas beamed at him, pulling the door shut and locking it behind him. "Are we traveling by foot or would you like me to drive?" He responded, and Dean's mind flashed to long drives with the windows down, Cas behind the wheel.

"I didn't realize you had a car! But nah, I made sure this was all walkable, if that's okay." He turned, leading Cas back down the street. He tucked away the road trip idea for a couple months down the road if things worked out. He hoped they did.

For much of the walk, Dean questioned Cas on his travels, his favorite places and what not. Cas was wound up in a story about working in Manhattan when they turned the corner to Pike's Place Market and he skidded to a halt.

"No way" Cas breathed, eyes flicking to Dean before launching forward. He floated between different booths, chatting with both civilians and shop owners, pointing and pulling Dean along. Dean had been here plenty of times, a frequent stop in his childhood. The place had become a tourist attraction in more recent years, but it was still fun and nostalgic to spend the evening. He couldn't help watching Castiel with a smile glued to his face, seeing the curiosity and joy in the man's eyes. Dean thought it looked good on him, and even more he liked that he had helped put it there.

As Dean had expected, Cas was enjoying the food booths throughout the market, putting together a makeshift dinner for the two of them. Dean waved off his other dinner plans, content to let his date explore more. They could grab drinks later, or maybe even plan dinner for another night. The idea thrilled Dean. 

The sun started to go down and Dean was able to drag Cas out into an open area just in time to catch the sunset. Colored light reflected from the clouds and the water made the sky look explosive, and in the excitement of the evening, made Cas gasp. Dean found he was staring at Cas more than the view. 

"Isn't it incredible," Cas began, not taking his eyes off the setting sun, "that every single day, in every single place, this view is different? I've been so many places and still there are sunsets that just inspire awe.." He trailed off, turning his gaze to Dean and finding the man staring up at him, a soft smile on his lips. Dean watched as Cas's cheeks flushed, and slowly reached out to take his hand.

"I'm finding that you're pretty incredible yourself, Cas." Dean said, his voice soft, eyes never leaving the piercing blue staring back at him. Dean would have liked to have kissed him then, but he was all too aware of just how many people were around. He didn't mind being in public like this, but this was a little too public for his comfort zone. He settled for gently stroking his thumb across Cas's knuckles.

"So, how you feeling? Hungry again? Drinks? Whatever you'd like, I'm yours for the night." Dean said after a moment, face splitting into a grin. 

Cas looked around speculatively before answering, "Drinks sound good, but you'll have to pick the spot."


	27. Chapter 27

Cas felt like he was in heaven. Cloud nine, living in a dream, all that. The more time he spent with Dean, the more he felt like they had known each other for years. It was just _easy._

After their date to Pike's Place, Cas had volunteered to walk Dean home for a change, and was treated to an impromptu make out session on Dean's couch before heading home for the night. He had wanted to stay, and got the feeling Dean wanted him to also, but he wanted to take this slow for now, even if it meant going backwards a little. He made a quiet promise to himself to stay a little longer next time.

 _Next time._ The idea thrilled him. 

They had chatted briefly over text on Sunday, making tentative plans to spend a day together next weekend. On Monday, Cas left a note on Dean's desk with his coffee: _Lunch?_

At lunch, Cas managed to swipe the bill before Dean could pull out the company card, a smug smile tugging at his lips when Dean narrowed his eyes at him. Did that count as a second date?

Throughout the week, Dean called Cas into his office for help with paperwork or calendar questions. Only, when Cas stepped inside, Dean would push him up against the desk, grinding into him and tangling his fingers in Cas's hair as he pressed their lips together. 

There were moments when Dean was soft, the look in his eyes similar to the one he had when they had watched the sunsets, and other times when the man was ravenous for Cas's lips. Either way, Cas felt like he floated through each day. 

It didn't take long for Balthazar to catch on, him and Gabriel cornering Cas at the elevators one morning until he agreed to talk with them over lunch. Cas knew Dean was still hesitant, even if he didn't say it out loud, and so he was sparse with the details. Gabe understood why Dean would be so apprehensive, making sure to convey the seriousness to Balthazar before he went spilling to the whole office.

Saturday came, and Dean had suggested they go out for brunch before another day of exploring. It was overcast, but warm, and the pair made their way to a spot downtown called Hell's Kitchen Table, notorious for adding a bit of spice to just about any of their plates. Dean ordered a giant breakfast platter- bacon well done, eggs over easy, extra hash browns- while Cas got a roasted red pepper omelet. Dean was most definitely not a morning person on days when he didn't have to be, but managed to liven up once he had food and coffee in him. Cas let him adjust, finding his sleepy expression endearing even if it was nearing noon.

After taking the time to digest their giant meal, Dean suggested some sight seeing. At this point, Cas was content to do literally anything Dean suggested, chatting with him about their lives, childhoods, local sights, anything. It nagged at the back of Cas's mind that Dean had yet to bring up Benny, as this thing between them was going on a couple weeks now, but it didn't feel right to ask. Not yet anyway.

They came up on the Space Needle in the early afternoon, both men standing below it and craning their necks to see the top.

"I'm not a huge fan of heights, but if you want…" Dean mumbled, eyes wide as he stared at the building almost shrouded by clouds.

Cas shook his head with a laugh, "No, no, no. I don’t do well with heights either. I've found I live easier with my feet on the Earth." 

"Okay, awesome. Then Plan B!" With that, Dean grabbed Cas's hand and turned him back the way they came. "I think you'll like this better anyway" he said with a grin.

Cas's heart beat a little faster as they walked and Dean didn't pull his hand away. He was talking about something, the pacific north west lacking in ocean views, but Cas was watching the way he moved his free hand when he spoke, the way his eyebrows shifted restlessly into various facial expressions, the way his hair blew in the slight breeze. The way he claimed he knew what Cas might like to do in his spare time, and how he wanted to be a part of it.

Suddenly Dean was turning, a smile spreading across his face as he met Cas's awestruck face, and gestured out behind him. Cas's eyes followed his hand to find they were standing at the edge of the water in a park that spread along the shoreline in either direction. The salty ocean air blew over them as they looked out at endless blue under endless, well, gray right now. It was beautiful anyway, a view so unobstructed it made you want to run toward it.

"Wow" Cas breathed, smiling as he dragged his eyes from the water to Dean, who was standing smugly beside him.

"It's not a tropical beach, or really a beach at all, but it's beautiful I think." Dean responded, glancing briefly at their intertwined fingers before looking back out over the water. 

"Dean, thank you. For taking the time to spend this time with me, doing all the touristy things you probably find rather lame, I-"

"What? No!" Dean cut him off, "No I'm actually enjoying kind of rediscovering this place with you. I haven't really spent time doing this stuff since I was a kid, really. I used to come here all the time, I don't even know why I stopped…" he trailed off for a moment, eyes unfocused as Cas watched him slip into his memories. He shook his head, turning back to Cas, "I like showing you. I enjoy spending time with you."

His cheeks flushed a little and he cast his eyes down, but Cas was quick, catching his chin and lifting it back to let their eyes meet. He smiled, "Well, thank you. I enjoy spending time with you too." He chanced a glance at Dean's lips, which were quirked up in a smile, then glanced around. He could tell Dean was apprehensive about their PDA in crowded places, but here they were almost alone…

He had barely brought his gaze back to Dean's when the man surged forward and pressed their lips together. Cas unlaced their fingers and brought his other hand up to cup Dean's other cheek, Dean's arms finding their way around his waist. The kiss was slow, and soft, and… wet.

Very wet, suddenly, as the skies opened up above them with the storm they had been holding back all day. The kiss broke with a yelp from both of them as they uselessly tried to shield themselves with their arms. Drenched in seconds, they sprinted for coverage under a cluster of trees. It didn't help much, but it allowed them to pause and erupt in laughter. Cas reveled at the way Dean's eyes bunched together in the corners, his head tossing back as he ran a hand through his damp hair. Cas thought briefly he would like to make Dean laugh like that.

Dean reached out and pulled Cas quickly into him, pressing their lips together hard for just a moment. "I guess I should have come up with a Plan C, huh?" He mused. Pausing for a moment to think, he placed a quick peck on Cas's cheek. "Let's get us dry, alright?"


	28. Chapter 28

**Summary for the Chapter:**

> This chapter is rated R

Dean hadn't planned for the day to end this way, a rookie mistake as most Seattle afternoons ended in rain. Part of him didn't mind where things were going, but a larger part of him was anxious as all hell. When he'd suggested getting dry, he hadn't given a second thought to calling an Uber for them to get back to his apartment. But now that they were soaking wet in the backseat of a black Honda, just a block from his place, he was worried it had been the wrong move.

Once inside the door, his brain began to scream for a hot shower. Normally that wasn't an issue, but now he had this maddeningly attractive and soaking wet man shivering next to him. 

"Uh, so if you want take a shower or I can lend you some dry clothes…" he wasn't sure what Cas would want. 

Cas shivered, glancing around the apartment before meeting Dean's eyes, "Do you want to shower?"

It was a normal question, but Dean felt the heat spring to his cheeks, "Well, uh, yeah I mean, I would usually, but.. If you, you know, I can wait till you.. Do whatever.." He rubbed the back of his neck, looking away from the eyes that were slowly narrowing at him.

"Dean Winchester" that god damn sex voice rumbled at him, drawing his eyes back up. He watched as Cas started to slowly unbutton his shirt, never looking away from Dean, "If you expect me to get into your shower _alone_ and not think about you waiting outside the door the entire time" he took a step closer, into Dean's personal space, "you have much stronger will power than I." Cas threw his shirt to the ground and caught Dean's lips in one swift movement, backing him up against the nearest wall.

Dean exhaled with a grunt as he hit the wall, his hands searching for purchase on Cas's damp skin. Cas, on the other hand, had grabbed a hold of Dean's flannel and was peeling it off his shoulders, using his other hand to pull his t-shirt off after it. Once Cas had Dean bare chested in the foyer of his own apartment, he began traveling across Dean's jaw, sucking in an earlobe and eliciting a soft groan from Dean. Dean felt fingers rake down his, torso, hesitating to rub a small circle around one of his nipples, forcing a whimper from his lips. Cas pulled back to meet his eyes, _hungry_.

"So, about that shower?" Cas smirked, and Dean all but sprinted toward the bathroom.

Last time, Dean had ravaged Cas, leaving him semi-clothed and wrecked in his office bathroom. This time there would be nothing separating them, and so Dean let Cas take his time peeling the damp jeans from Dean's legs, breath catching in his throat as he watched his dick spring loose inches from Cas's face. Cas let his hand trail up Dean's thigh as he stood, fingertips brushing his dick before wrapping around it. Dean let out a gasp, locking eyes with Cas as he stroked him a couple times.

Cas smirked, pulling away to take off his own jeans, never breaking eye contact as he stroked his own dick in front of Dean.

_Fuck_.

This guy could play nerdy secretary, but when he got in this mood, he was a whole different animal. Dean couldn't get enough. 

He pulled Cas in the shower with him, exhaling as the steam beat the chill of rain from his shoulders. He let Cas step into his personal space, pushing him back against the shower wall as he moved for Dean's neck. Dean gave in then, releasing all tension from his body and relinquishing control to Cas. As if he could feel it, Cas moved to capture Dean's wrists in one of his hands and raised them above their heads, pinning him to the wall. His free hand on Dean's hip, their bodies slipped together and he continued to explore Dean's upper body with his mouth, sucking small bruises along the man's collar bone before dipping his head farther down. Cas caught one of Dean's nipples between his lips, and Dean began to crumble.

He could feel Cas smirking as Dean whimpered, and he could feel Cas's hand slip from his hip to find his dick, stroking him as he sucked and licked, Dean not able to hold back from moaning and writhing in Cas's grip. 

Cas pulled away suddenly, catching Dean's eyes as they fluttered open, letting his arms fall to his sides, before sinking to his knees in front of Dean. _Christ_. Mischievous blue eyes looked up at him as Cas's mouth closed around his dick, and it took everything in Dean's power not to squeeze his own eyes shut. He watched, lips parted and panting, as Cas took him in as far as he could, licking up and down his length while his head bobbed along. Dean could feel the burn building low in his stomach. He reached his hands out to tangle them in Cas's hair. 

"Cas, oh, _fuck_ " he groaned, thrusting a little to meet Cas's mouth. "Cas I'm, I'm _guh_ -" his orgasm hit him like a punch to the gut, his mouth wide but silent as Cas drank him in. Cas sucked slowly, helping him come down before pulling his mouth off and standing to hold Dean up.

Dean hadn't realized how much sexual tension he had let build up over the last few weeks, he was exhausted.

"You.." Dean breathed, earning a chuckle from Cas.

"Later." He mumbled into Dean's neck, reaching behind him to turn the shower off. "Come on, where are towels?"

Dean vaguely remembered they were at his place, and so he shook his head to clear his foggy thoughts, pushing himself from the wall in search of towels. 

A few minutes later he found himself horizontal on the couch, head still a little foggy, with a warm and mostly dry Castiel curled up next to him. Both were wearing Dean's sweats, the TV playing quietly in the background. Dean mindlessly kissed the top of Cas's head. "How do you feel about some take out?"

**Notes for the Chapter:**

> In the last couple weeks I have gotten a lot of incredible, positive, and encouraging feedback and I just wanted to say thank you all so much! Thank you for bearing with me and my irregular posting schedule, and continuing to follow along anyway.


	29. Chapter 29

This wasn't at all how Cas had expected this day to go. He wasn't upset though, not in the slightest. He watched over the arm of the couch as Dean paced mindlessly through the kitchen while he was on hold with the Chinese food place. _Best in town_ , he'd told Cas.

Cas couldn't help but stare. Dean looked fantastic in just about anything, a suit at work or casual clothes when they'd gone out, but Cas mused that this look had to be his favorite. He was leaning back against the far counter in the kitchen, arms crossed over his bare chest, gray sweats hanging low over his hips. His hair was a little unruly from a quick towel dry, cheeks still a little pink from the heat of the shower. Cas found himself thinking Dean bumming around in the kitchen was something he could get used to. Dean doing anything was something Cas wanted more of.

His cheeks began to burn as his eyes trailed up Dean's body and met the smirking green watching him. Cas realized that here, he didn't have to tear his eyes away in embarrassment, so instead he held the eye contact and allowed a smile to play across his lips. Yep, he could definitely get used to this.

They relaxed on the couch until their food arrived, Dean- to Cas's disappointment- pulling on a threadbare t-shirt to get the door. Dean dragged Cas off the couch and into the kitchen to eat at the counter, the pair sharing casual conversation until they were too full to speak. The storm continued with an unforgiving ferocity outside, but Dean made no moves to suggest Cas head home. Instead, he suggested a movie.

Dean insisted on a favorite of his, Tombstone, since Cas had never seen it before. Afterward, still lounging on the couch, they talked about other favorite movies, making an impromptu To Watch list for future rainy days. Cas's chest felt warm, full, with the prospect of doing this more often.

It was late now, and even though he didn't want to, Cas began gathering his things to leave while Dean ran to the bathroom. His clothes were still damp and it was still pouring outside, so he decided calling an Uber would be better than walking the couple blocks. When Dean returned from the bathroom, he caught Cas's arm.

"Hey, whoa, you sure you want to brave the storm? It's been a while since it's been this bad out."

Cas smiled, appreciative of the small caring gesture, "I don't want to take over your whole weekend, Dean. I should go."

Dean's brows furrowed as he considered Cas, nibbling slightly on his lip. His hand slid down Cas's arm to brush their knuckles together. "You could stay… if you want.." He mumbled.

"Dean, I-" _would absolutely love to spend the night with you,_ "It's fine, I don't have to."

"I want you to stay" Dean blurted out, eyes looking anywhere but at Cas as he continued to chew on his lip.

Cas paused. This day had been so much fun, doing almost nothing with Dean. Who knows what tomorrow would bring, but he was eager to find out.

"Okay. I'll stay." Cas said. 

***

Cas changed into his boxer briefs in the bathroom before going to Dean's bedroom. It was odd, coming into a bedroom for the first time to actually _sleep_ rather than sleep together. The sound of rain outside the open windows, the soft light spilling in from the streetlights, the soft rustle of sheets and blankets, it seemed more intimate to Cas than falling into the bed in a tangle of naked limbs.

"Hiya, Cas" Dean breathed once Cas had settled in.

"Hello, Dean" Cas said in a low rumble across the few inches between them.

A beat of silence, where Cas saw Dean's lips tug upward as they stared at each other, then Dean was shimmying himself into Cas's space. Dean nuzzled at Cas's jaw, trailing his lips up to his ear while he wound his arms around Cas's waist. "I think I owe you a favor from earlier" he breathed in Cas's ear.

Cas's eyes widened, a flush spreading across his cheeks as the tickle of Dean's breath shot through every nerve in his body- right down to his dick. At this proximity, there was no way Dean _hadn't_ felt the eager twitch against his leg. It was, apparently, the green light he had been hoping for.

Cas's breath hitched in his throat as Dean rolled him onto his back, crawling over him and starting the slow descent down his body with his lips. He felt Dean's hand skim over his crotch, fingertips trailing teasingly over the fabric separating them. In the same moment, Dean's teeth grazed across a nipple and Cas couldn't help but buck underneath him.

Feeling Dean smile against his chest, Cas managed to open his eyes to glare down at him. Dean waited until their eyes met before he dove his hand into Cas's boxers, wrapping his hand around his quickly hardening dick.

_"Ooohh"_ Cas moaned, head falling back against the pillows. His hands found their way into Dean's hair as he resumed his path down Cas's torso, grabbing small handfuls with each stroke.

With his free hand, Dean tugged Cas's boxers lower to completely expose him before dipping in with his mouth. Cas craned his neck, eyes straining as he watched Dean turn his head to mouth at his dick while his hand continued working him slowly. He whimpered, wanting Dean to take him in fully, wanting to flip them over and take Dean himself. Instead, he let himself be pleasured, watching through hooded eyes as Dean dipped to give a hesitant lick to his balls before letting his tongue trail up this length.

Cas made a mental note that Dean was maybe a little apprehensive about being intimate with a man, despite what Cas knew about his past. He wouldn't question it, but would happily reassure and guide Dean if needed. 

Letting his head roll back in pleasure, he gasped and moaned through the rhythmic pumping of Dean's hand, the gentle licking of his tongue. He wasn't going to push Dean to do more than he wanted, but he needed more. Slowly, Cas began pushing his hips, fucking himself up into Dean's hand. He felt Dean's breath in a short puff against his dick as he pulled his mouth away to watch. Cas glanced down then, eyes going wide as he watched Dean stroking himself with one hand while Cas slowly fucked himself into the other.

"Dean" he choked, getting impossibly harder at the sight. He launched then, off the bed to roll Dean onto his back as he took him into his own hands. Cas's mouth found Dean's with a crash, swallowing the whimper that escaped as Cas began to jerk him off.

"Cas, Cas" Dean breathed, breaking free from the kiss, "Let me."

Slowing his hand, Cas considered this. He was, and always had been, a giver. He liked watching his partners fall apart by his doing. But Dean wanted to do that for him, who was he to deny the man.

He smiled, swooping in for a quick kiss before sitting back. "Sorry" he mumbled, "I couldn't resist."

Dean looked him over in the dark, seemingly forming an idea. Cas tilted his head, about to question him, when Dean surged forward, stopping the question in his mouth. Arms wrapped around Cas's neck, Dean crawled in his lap, straddling him. Cas's heart rate quickened at the prospect of what Dean was doing, but his mind shifted gears as the man in his arms settled down on his haunches. 

Dean unwrapped an arm and slid it down to take Cas's hand, guiding him to wrap around his dick, then wrapping his own hand around Cas. Stroking each other, their mouths met with soft gasps. Cas's free hand wrapped around Dean's back to keep him steady, pull him impossibly closer, as Dean's free fingers tangled their way into the hair at the back of Cas's neck. Between kisses escaped quiet moans, the occasional whimper, and the shudder of breath as they worked each other closer to the edge.

"Dean" Cas's voice came out ragged, wrecked by the perfect, quiet intimacy of the moment, thoughts liquifying as he felt himself tumble into orgasm, _"Dean."_

Dean let out a low groan in response, trying to stroke Cas through his orgasm while he rode out his own, head rolling backward. After a moment he pulled his head back up, resting his forehead against Cas's. Cas blinked, trying to refocus his eyes, inhaling sharply when they did. At this angle, Dean's flushed cheeks brought out a brilliant spattering of freckles visible through his long eye lashes. Cas smiled to himself, lifting his chin to press a soft kiss to Dean's cheek.

Eyes fluttering open, green met blue and they smiled. Dean caught Cas's lips in a quick kiss before untangling himself to find a means of clean up. A few moments of soft chuckles and shy kisses later, and Cas found himself wrapped around snoring Dean's back, slipping into sleep with a smile on his face.


	30. Chapter 30

Dean woke wrapped up in Castiel. For a minute he let himself take in all the little details. Cas's lips, dry and pink, parted slightly exhaling little puffs of breath, his cheeks rosy with sleep, hair sticking up in every direction. As Dean stirred, Cas rolled onto his back, nestling into the pillow without ever opening his eyes. 

Reluctantly he dragged himself up and went about getting a slow start to the day. He freshened up, peeking back into the bedroom to see Cas still passed out, and headed to the kitchen. It wasn't often Dean got to cook for someone, and this was the perfect time to take advantage. He started up the coffee maker, pulling out the rest of the sample coffee Sam had sent him, then got to work gathering breakfast ingredients. Halfway through mixing up some cinnamon roll waffle batter, Dean heard the soft shuffle of footsteps.

With a grin, he turned to greet Cas, "Good morning, sunshine!" Dean poured Cas a cup of coffee, and refilled his own mug before sliding onto the bar stool next to him. "How'd you sleep?"

Cas took the coffee gratefully, wrapping his fingers around the warm mug, "Like the dead" he mumbled, and Dean appreciated that Cas's morning voice had even more of a rumble to it than usual.

"Well, hope you like waffles, I'm making a specialty." Buzzing from his first serving of coffee and digging eagerly into his second, Dean hopped off the stool and back to his mixing bowl. After a few minutes, Cas was awake enough for conversation. Dean noted that his cheeks were still rosy and his hair still a mess, and he looked awfully cute when he was just waking up.

Over waffles, with a side of bacon ( _It's not breakfast if there's no bacon,_ Dean insisted), they discussed their plans for the day and coming week. The air had a slight chill, drizzle still coming down as the aftermath of the night's storm. Dean was in no rush to let Cas leave, but understood the man probably wanted his own clothes and some time to himself. 

Cas helped him clean up, both men slipping in a few flirtatious touches, smiling and glancing at each other as they moved about the space with ease. Cas changed into his now dry clothes from the day before, and as noon approached Dean found he was searching for things to talk about to prevent him from leaving. He was enjoying the company, but also the casual familiarity with which they interacted. Rubbing the back of his neck, Dean walked Cas to the door. He didn't want this to feel like a one night stand kind of goodbye because he didn't want it to be a one night stand.

"Thank you for breakfast, Dean. And for yesterday. And uh, last night." Cas said, cheeks flushing a soft pink.

"Hey, I'm glad you enjoyed it. Um.." Dean cast his eyes down to his feet, "Uh, if you want, I mean if it's something you would like, maybe I can make us dinner sometime? Maybe this week?" He felt his own cheeks flush. God he was such a wimp! "Or if you'd rather go out somewhere or do something else or-"

"Dean" Cas cut in, "I would love for you to cook for me. I'm not so great myself, maybe you can even give me a few pointers." He met Dean's eyes with a smile, and Dean beamed right back.

"Awesome, yes, absolutely" he replied.

They stood there grinning at each other for a moment, then Cas leaned forward to catch Dean's lips in his. He let them linger, and Dean could feel the twitch of a smile, before he pulled away and reached for the door.

"I'll see you tomorrow, Dean" Cas said, and Dean's heart did a little skip.

***

 

Dean didn't really mind that people at the office noticed his change in attitude. He could tell he was smiling more, he was friendlier, he came out of his office more often. When he could he would steal a moment with Cas, just a quick look or a kiss in the elevator. He wasn't sure if people knew, but he didn't care. If they wanted the facts they could talk to him about it, this wouldn't be like last time. 

On Wednesday, he made chicken pesto pasta for dinner with Cas. Cas watched, eyes narrowed and head tilted to the side, from a safe distance, asking some questions but mostly mesmerized by the way Dean danced around effortlessly as he cooked. They ate with bread and wine, and collapsed on the couch giggly, full, and attached at the lips when it was over. The next morning, Dean lent Cas a fresh shirt and hung around outside the office to give him a head start, not realizing till much later that their matching hickeys probably gave them away.

On Friday, they let themselves get dangerously close as happy hour with the team came to an end, earning an eyebrow waggle from Charlie and a couple comments from Balthazar. Gabriel smirked, a seal of approval, before they left the bar to stumble their way to Cas's apartment. Dean found the studio cozy and charming, and all the windows kept the space nice and cool as they tangled themselves together on any piece of furniture they could find. They enjoyed coffee in bed the following morning, not crawling out from the sheets until the early afternoon.

And so this was how things went between them. Torturous days at the office, nights where Dean cooked and Cas watched, or Cas tried to cook and Dean eventually took over, the occasional sleepover followed by lazy, quiet mornings. They fell into a pattern, every moment spent together reassuring Dean that despite his past mistakes, he could open himself up and be with someone again, and even more, that he _deserved_ to be with someone and be happy again. They grew comfortable with each other, with their semi-secretive lifestyle, and they were happy together.


	31. Chapter 31

Cas was falling for this guy, his own boss, and nothing could stop him. The little routines they had worked out together, the way they moved with and around each other like a practiced dance, the way they fell into such a fluid rhythm. Cas often found himself dumbfounded that he could be so lucky.

But there was just the one thing still whispering at the back of Cas's mind after these couple months.

It was a Friday evening, and Dean had suggested skipping out on end of week drinks in favor of going home (Dean's home, although sometimes Cas caught himself calling it home as well) to make a nice dinner and watch a movie. Dean had pushed Cas from the kitchen, declaring he needed to be alone for something so extravagant, and so Cas found himself on the couch. He was half flipping through channels and half watching Dean in awe as he floated around the kitchen humming to himself.

That's when Dean's phone buzzed on the coffee table in front of him.

Cas glanced at it, nothing more than instinct upon seeing an illuminated screen, but froze instantly. 

**Benny** \- 5:52 pm  
 _Hey there handsome, you around for a little fun tonight? Been missing you_

After the initial shock of the whole thing, Cas's mind began racing. Why was Benny texting Dean? Did this happen often? Hadn't Benny left town?

Why did Dean still have his number?

Cas could feel his face getting hot as his brows furrowed in concern, not sure how to proceed. Dean didn't know Cas knew about Benny, so for him to bring it up would lead to more of a mess. But he couldn't ignore this, could he? He had never made things official with Dean, so maybe that meant Dean was seeing other people. But this wasn't just other people, this was his _ex,_ the one who had royally screwed Dean and almost his whole company. _Why_ would they still be in touch? And talking about _having fun?_

He was snapped back into reality as Dean slid a giant plate down in front of him. As Cas collected himself he focused on the giant pizza -- had Dean made them a giant pizza?

"Ta-da!" Dean exclaimed, gesturing widely with his arms in presentation. Cas smiled up at him, but even he could feel it was weak. His head wasn't here anymore, enjoying a quiet night in with Dean, but yelling at the back of his mind to jump ship.

Dean instantly noticed.

"Hey, you good?," he said, flopping down next to Cas and placing a hand on his shoulder.

"I, uh.." Cas struggled to figure out what to do. "I don't feel very good all of a sudden."

Dean's brow furrowed, "Do you want to go lay down? Or some water? What can I do?"

Dean's eagerness to care for him stung a little, as Cas couldn't fathom caring for someone so deeply and failing to mention something so dire.

"I think I have to go home." Cas stated bluntly, standing and gathering his things. He could see Dean falter out of the corner of his eye. He knew he should be addressing this rather than running, but he needed to just process first. 

"Oh.. Okay." Dean's voice sounded small. "I get the vibe you don't want me to walk you…" he trailed off, fingers twisting together anxiously.

"I'll be fine, thanks," Cas said, hesitating by the door, "I'll um, talk to you later." And he bolted, without giving Dean a chance to respond.

***

When he was outside, he called Charlie. Charlie was the only person that had grown to know both of the fairly well, and he needed her input as far as Dean's side went in this.

He heard her moving away from the noise of the bar during happy hour as soon as she processed the serious tone of his voice, and then he told her everything. How Balthazar and Aaron had spilled the big secret to him when he first started working there, and how he hadn't really cared until Dean came into the picture, and Dean and never brought it up and now Benny was texting him and Dean was still sleeping with him and he was so stupid to ever--

"CAS" Charlie's voice broke through his ramble, "Hey man, slow down. I'll be at your place in twenty."

He took a deep breath as he hung up, continuing his walk the couple blocks to his studio. He wondered if Dean would call, or if he should call to clear the air, or if Dean would go see Benny now that Cas had left for the evening.

His mind continued to over think the rest of the way home, and for the remaining time he sat staring at nothing in particular as he waited for Charlie. She let herself in, immediately going to the fridge and grabbing a couple beers. This conversation would need it.

He started from the beginning, the conversation over drinks with Balthazar and Aaron, and everything Benny related that had (and had not) happened afterward. Charlie listened, and Cas could see she was equally as confused about the text. That only worried Cas more.

"Benny is…" she trailed off, struggling to find the right words, "Kind of lacking in empathy. When everything happened, we found out that the Benny we knew wasn't who we had thought, and he was actually selfish and uncaring. That hit Dean especially hard since… you know… but everyone else felt it too. We were all friends and he had just been… lying." She paused, her eyes distant as she recalled her memories of Benny.

"So I guess, it would make some sense that he would still go to Dean for, I'm sorry, a booty call. He wouldn't care what that might do to Dean or to the people around him, since he's only thinking about himself." Charlie finished, taking a long swig from her bottle and she continued to think.

Cas exhaled, "I just don't understand why he would even still have Benny's number."

"Honestly Cas, I don't know why either. But you have to talk to him. You guys are too much of a good thing to let some crappy guy like Benny screw it up."

Cas blushed, smiling slightly at Charlie's approval, before frowning at the thought that this could be over and it would be on him. "I suppose I'll sleep on it and talk to Dean in the morning."


	32. Chapter 32

For a few minutes, Dean sat in silence on his couch going over every interaction he and Cas had since they had walked out of the office just an hour or so ago. Was Cas mad that he had shooed him from the kitchen? It had just been a joke, this stupid pizza he always made for himself on nights when he couldn't be othered with other people, he'd never shared it with anyone else and well… now he wanted to share it with Cas. Whatever. Maybe he really hadn't felt good, but still…

He picked up his phone with every intention of sending Cas a quick text and immediately calling Charlie, when he noticed a message from Benny. Sighing, he opened the message, revealing the thread of previously unanswered messaged from the last time Benny had been in Seattle a few months ago. He rolled his eyes, thumbing back through messages to find Cas's thread when he started to process the thoughts lingering at the back of his mind.

He went back, checked the time stamp, checked the clock. Shit.

There was no way Cas would know who Benny was-- or had been-- to Dean, but seeing that message with any name attached was probably not a good thing. He let out an aggravated groan as he tossed his phone and dropped his head into his hands. In a perfect world, Benny would have never come up and his relationship with Cas would continue to be quiet and wonderful.

Did he just say relationship?

Dean felt the cold seeping of paranoia in his gut as his mind suddenly began spewing all the things Cas would think about him for what he did to his own company, for being so stupidly blind, for getting into something with Cas when it was so similar, did he do this all the time?

He stopped himself, squeezing his eyes shut and taking a deep breath. Cas was nothing like Benny. What he had with Cas was nowhere near similar, it was so remarkably different and Dean was happy for the first time in a long time. Even if they hadn’t put a label on themselves, he wanted to keep this thing going.

Grabbing for his phone, he swiped to ignore yet another message from Benny and headed straight for Cas.

_'Hey babe, hope you made it home okay. Coffee in the morning?'_ He sent, then settled in to enjoy his pizza and clear his mind.

***

Cas had responded a little bit later agreeing to coffee, and so Dean had planned to call Charlie for advice on how to handle this when it occurred to him he hadn't told Charlie that he still heard from Benny. In fact, he had flat out lied and told her the opposite. Charlie would understand when he had a chance to explain it all to her, he hoped, but now he was walking into this coffee shop without a single clue how to approach the situation.

He spotted Cas almost instantly, feeling the intense blue gaze before he met it, and smiled. He couldn't help it. Cas was wearing a hoodie and jeans, his hair tousled in a way that said he didn't want to be out of bed yet. Adorable.

"Hey, how are you feeling?" Dean asked, sliding into the seat across from Cas.

"Fine now, I think I just needed some sleep. Long week, I guess." Dean noticed Cas was looking down at his hands now, fiddling nervously. 

"Let me get us some coffee." Dean suggested softly, quickly brushing his hand over Cas's in hopes of comforting the man a little. It was beginning to make Dean equally as nervous.

When he came back, sliding a mug of lighter coffee in front of Cas, the other man still wouldn't look up at him. Dean hesitated, unsure where to began, when Cas suddenly cut him off.

"Why are you still talking to Benny?" He blurted out, his expression changing suddenly to one of panic as if that wasn't what he had intended on saying.

"I-" wait, what? So Cas did know who Benny was. Fuck. "How do you know who Benny is?" Dean asked slowly, trying to sift through his memory to a time it might have come up. No, he would remember.

Cas's face flushed and he cast his eyes back down. "I um, some of the other employees were talking and…" he trailed off. Dean's jaw tightened as soon as the sentence was out of Cas's mouth, his eyes no longer soft and inquiring but hardened. Why the fuck couldn't people keep their mouths shut.

"They don’t know what the fuck they're talking about" He spat, the anger in his voice causing Cas to look up at him once more. His eyes narrowed, he looked almost confused.

"Dean, this isn’t about them. I don’t care what happened, I just want to know why he's still talking to you." Cas said slowly, pausing before he continued, his eyes back down on the table, "I just want to know if this is what I thought it was."

Dean froze, the anger and paranoia bubbling in his gut. What was this? What was he doing? He promised himself he wouldn’t do this ever again and now here he was, on the verge of talking about feelings with what, his secretary? Again? He felt his mouth opening and closing, trying to decide on what to say next. He could end this right now, save himself the embarrassment of the world eventually finding out again, of having to explain himself, of Benny coming forward and costing him his job. Was this worth it? Hell if he knew. A tiny voice at the back of his head screamed that Cas meant happiness, but what was happiness if he lost everything he had worked so hard for. For his damn _secretary._

The sudden scratch of chair legs against the floor brought him back, and he realized he was staring at an empty chair, as Cas moved around him to head for the door. He jumped, surging after him, leaving his untouched mug of coffee on the table.

"Cas!" He yelled, once outside. He watched Cas pause, contemplating letting Dean explain his inability to answer a simple question, but it seemed he decided Dean wasn't worth it, and continued on down the street. Dean didn't want to cause a scene, running after him yelling like some stupid romantic comedy, but he didn't want him to go either. 

The paranoia in his gut reached full strength and he realized he was more worried about losing Cas than the world finding out his deep dark secrets. He hadn't explained anything to Cas at all, and now he was walking away and clearly didn't want anything to do with Dean anymore.

When he looked back up, Cas was gone. Fuck, what had he just done?


	33. Chapter 33

Cas made it safely inside his studio before he let the tears start to fall. So he had just been a play thing on Dean Winchesters to do list. He meant no more to him than the last secretary he had fucked, and he had been stupid to think otherwise. Dean was the typical CEO, doing whatever he wanted with whoever he wanted, and Cas fell right into the trap. He was so stupid.

Pulling himself together, Cas made a decision. It wasn't like this job would last forever, and what better time to get out than right now, when you've been sleeping with the boss and it turned out you meant nothing to him. As he threw some clothes into a bag, he pushed down the thoughts of watching sunsets and getting caught in the rain and let the ones of Dean gaping at him as if he didn't owe him any explanations take full reign. Double checking the lock on the door, he made his way to his car. He'd be back when he found his next gig to collect the rest of his things, but for now he just needed to get out.

***

Later that evening, sitting at a dive bar in Portland, his phone went off. A phone call from Dean. He let it ring, already a couple drinks in and in absolutely no state to deal with this.

He was staying at a motel around the corner tonight, and had plans to take himself out to the coast in the morning, hopefully getting into warmer beach weather in the next couple days. Maybe Seattle had turned him gloomy and some beach side living was the cure he needed.

Dean called three more times. He turned his phone off.

***

As expected, when Monday morning came, his phone lit up with messages from his coworkers, well ex-coworkers now, at Winchester Roasted HQ. If he was being honest, what he wanted right now was a couple of drinks with Balthazar to rant about everything that had happened. Being alone the last few days, his mind had spun stories of what Dean might have said, how he was spending his time without Cas, if he had already found someone else. He remembered all the times Dean acted different in front of other people, all the times he had hid Cas from everyone else. That wasn't what people in relationships did.

Well, they hadn't really ever been in a relationship, had they?

He quickly typed out a reply to Balthazar and went back to his book. Ironically, the rain had followed him down the coast, as if tell him he couldn't just run away from this. He was parked along the water, curled up in the passenger seat with the window cracked listening to the waves and the soft beat of rain on the car. He thought about the way the rain sounded through Dean's windows at night.

He thought about what to say to Dean, if he decided to talk to him again. He knew he would, it was childish to just disappear like this, but he needed time. After this past month or so he had really started to feel something for the man, started to think about Seattle being more permanent, about _Dean_ being more permanent. Stupid, since he hadn't really known him after all. Why wouldn't Dean just talk to him? Open up about his past and they could go from there. It was like bringing Benny up had fried Dean's senses. If this had just been some fuck buddy that Dean had said a little bit too much too, well, who cares? Shit happened sometimes, there was no reason for Dean to get so emotional…

Something clicked then. He hadn't thought of it before since he had never seen Dean's reaction to Benny, but suddenly it made sense.

It wasn't just a good time for Dean like Cas had previously thought but… maybe Dean had actually liked the guy, loved him even. Cas felt his whole body go cold as he rearranged the pieces with that new information. Dean had thought they were together, Dean had told him secrets, and then he left and sold all Dean's secrets and now… Dean had felt used. Much like Cas had been feeling the last couple days. Dean had just been a pawn, or probably closer to a queen, in Benny's game. Getting with Dean, convincing him to spill company information, that had been the check mate. 

Well, shit.

Letting his head fall into his hands he let out a groan. He had screwed up big time if what he was realizing now was true, and there was probably even more to it than that. He could understand now why Dean hadn't explained himself, it probably hurt him too much. And with Cas, well, he was doing it all over again. But Cas had no ulterior motives, no secrets, he just wanted Dean. He felt a lump forming in his throat at the thought of never being able to express that to him again. What the hell was he supposed to do now?


	34. Chapter 34

When Dean had shown up to work this morning, it was obvious that something was wrong. He himself was a disheveled mess, but there was also a strange buzz around the office. When he got out of the elevator, his heart sank as he realized why.

Charlie stood by his door, eyes darting to the empty desk beside it. 

"Did he call out sick?" Dean croaked, his voice giving away a weekend lacking in sleep.

"Um, well.." Charlie hesitated, "Well he just hasn’t shown up yet," she said, hurrying to add the 'yet' in hopes of lifting Dean's spirits. It didn't work.

He sighed, hanging his head as he pushed through his office door and flopped into an arm chair.

"What did I do Charlie?" He mumbled, rubbing at his eyes.

She shook her head, glancing back through the frosted glass at the empty chair. "Have you heard from him?"

"He's ignored all my calls and texts, I just, I don't know what to do. I snapped, I deserve this, I just wish I had explained it to him and now he wants nothing to do with me all because of what everyone _else_ put into his head."

While Dean spoke, Charlie shot a quick message to Sam. 

_'Hey, did you manage to get a flight?'_

_'Sure did, I will be there after lunch.'_ Was his reply, and she smiled to herself. Sam could always make Dean feel better.

"I think you still have time to explain your side to him, Dean." She supplied, "And I don't think Cas is the kind of guy to jump to conclusions, he will listen."

Dean had called her on his way home from the café on Saturday morning, letting everything out, and she had understood just like he had hoped. But it was no longer Charlie that he needed to understand. In the time he'd had to think everything over, sort through his anger, his hurt, his sadness he had realized Cas was so much more to him than just a secretary, just another employee. They had become friends, more than friends, and Dean wanted so desperately to tell him how he felt and more.

"How is he going to listen if he won't pick up the phone?" He whined, and Charlie rolled her eyes.

"Dean Winchester, stop it. You know full well that when you really want something, you find a way to make it work. And I _know_ that you really want him. Just give him some time, he's probably hurt and frustrated… he probably feels a lot like you did…" she trailed off not wanted Dean to get angry, but in fact that seemed to get his attention.

"I don't want him to ever feel that way" he whispered, his voice cracking. He cast hopeful eyes toward the desk outside again, but still found it empty.

***

Charlie had taken him out to lunch in hopes of clearing his head and letting him have a productive second half of his day. It had helped a little, and as he strolled back into his office his heart lurched as he saw a man standing beside his desk. It only took a second to rule out Cas by the height alone, which could only mean…

"Sammy?" He gasped, emotions welling up as his brother met him with a grin. He all but ran to him, pulling him into the tight squeeze he reserved for Sam alone. "What are you doing here?"

Sam shrugged, pushing his hair out of his eyes, "Charlie said you could use some cheering up so," he stepped back, holding his arms wide to gesture at himself with a goofy grin. Dean cracked a smile. They had been apart far too long.

Dean glanced down, noticing the backpack and duffel at Sam's feet, and decided he didn't want a more productive day.

"Come on, I'm taking a half day." Dean said, gathering his things. Sam stopped him.

"That's totally fine, I just figured maybe we could bring this down to the tasting team," he grinned pulling a couple bags of his new coffee from his duffel. Deans eyes lit up with the prospect of a tasting led by Sam in person, and they hurried toward the elevator.

It had been wise of Sam to slip in while everyone was out on lunch, because now they were being stopped every few feet. Sam had been off traveling to coffee farms for quite some time now, and everyone was thrilled to see him and ask about his travels. Ever charismatic, Dean stood back and watched as he hugged his way through a growing mob of old friends, his laugh leaving a smile plastered to Dean's face.

Suddenly a soft hand on his shoulder. Gabriel. One of Sam's oldest and dearest friends. Dean cleared his throat causing Sammy to turn, his eyes lighting up when they landed on Gabe. It was always a funny sight, Sam being almost two times Gabriel's height, pulling him into an embrace. They talked excitedly, forgetting about everyone else, and Dean smiled. Sam made the office feel like a home again, when for so long it was just work.

A slew of employees followed them down to Tasting, where Sam met Balthazar, enthusiastic and flirty as ever, and he began to set up his tasting. Dean, Charlie, and Gabe hung at the back, eager to watch Sam spew all his newfound knowledge. Out of habit, Dean turned to whisper something to Cas, and felt a sharp pang in his chest when he realized he wasn't there. Charlie caught his expression, gently taking his hand.

He let himself focus on Sammy, whose eyes shown with childlike joy as he did what he did best. He let himself drift away from thoughts of Cas for now, knowing full well Sam would be on top of the situation as soon as they were back home. For now he welcomed a different happiness, the kind he felt around his baby brother.


	35. Chapter 35

Cas had thought about calling Dean several times since his epiphany the day before. He'd let his thumb hover over the call button, his mind suddenly racing with doubt. He could be totally wrong about the whole thing and end up making an even bigger fool out of himself. It was bad enough he was falling for his boss, but calling the guy up to discuss past relationships and their consequent feelings just seemed like it wouldn't go over well. Dean didn't talk about his feelings, and maybe it was because he didn't have any particularly strong ones about this _thing_ , or maybe it was because he had too many. It wasn't Cas's business to force that on him, either way.

So instead, he sat staring blankly at his phone in an empty café at 2pm on a Tuesday afternoon. He was acutely aware of the barista glancing over at him every few seconds, probably because he had come in and sat down without ordering anything, and was now just sitting there in silence. With a long exhale he hauled himself up and walked to the register.

The barista was a short, cheery eyed guy, with a little bit of scruff and some loose light brown curls. His nametag, precariously hanging from his apron, said Chuck. 

"Hey man! I was wondering if you were going to come up here. What can I get for you?" He smiled at Castiel as he spoke and Cas noticed the cheery attitude was a little contagious.

He smiled back, "Can I get a, uh, vanilla latte?" it had been a long time since he'd treated himself to something other than Winchester brand coffee. 

"Sure thing!" the man said, ringing him up before beginning to make his drink. Cas couldn't help but watch the way the guy moved, so sure of himself, around the machinery. It reminded him of watching Dean cook. He leaned over the counter a little, watching the milk steam into perfect velvety foam, the smell of the espresso mixing with vanilla filling the air. He smiled. This was a part of the coffee business he would love to learn.

Sitting in the café sipping on his latte, he fantasized briefly about stepping out of his life long role behind a desk and instead, stepping behind a counter, dawning an apron and hand crafting the small cups of perfection that his office dwelling coworkers worked so hard to put out in the world. Just out of curiosity he opened his laptop, doing a quick search for barista jobs in Seattle, and chuckled at the results. The Winchester Roasters shop, the one he and Dean stopped at so frequently, was hiring. 

He applied.

 

***

 

The next morning he woke to the vicious vibration of his phone under his pillow. Charlie was calling.

"Hello?" he supplied, sitting up and rubbing his eyes before he had a second to consider what this call might be about.

"Cas!" she nearly squealed and it occurred to him that he had ignored all her texts and calls for the last three days, "Can you talk for a minute?"

He sighed, knowing full well this would happen eventually. He curled forward, letting his chin rest on his knees. "Sure." he murmured.

"So um, as you know I'm in charge of hiring and employment and all that jazz," she was talking rather quickly, and Cas, still not fully awake, was squinting his eyes in effort to follow, "and so, well, I don't know how you feel about… remaining in your current position…" at this she paused, waiting for him to respond.

He sighed again. He loved this job, loved the people, but he couldn't keep working under Dean, whether things worked out or not. "I don't think it would be in mine or Dean's best interest for me to stay, Charlie." he could hear the sadness in his voice, but he had known from the start this wasn't going to last forever.

Charlie hesitated before continuing, "Are you… leaving, leaving?" 

Cas didn't have an answer. He knew in his gut he needed to talk to Dean, just like he knew he couldn't stay in this hotel forever. 

"I don’t know yet, I still have my studio and everything I just… needed some time to think." 

"Well…" she began slowly, unsure if she should continue, then jumped right into it, "well I'm in charge of hiring, like I said, and I don't know if you know this, which you probably don't because you don't work in this position, but all applications get sent through my office and usually I don't pay much attention because it's just so many people since the company is so big, you know? But anyway, so I don't usually pay much attention but because you're still in our system here at the office I got a flagged application for the Winchester Roasters that's just a couple blocks away…" she slowed again, trailing off, letting Cas fill in the missing pieces.

"Oh." was all he said. Well, it had been worth a shot to apply.

"If it means you staying local I can call their manager and pretty much give you the job right now. I know it's none of my business, but dammit Castiel, even if he's an idiot sometimes, he needs you. He's been a mess, please just call him. I won't say anything about the job, that we spoke at all." she paused, "Unless that isn't what you want."

Cas's breath caught in his throat. His whole life, traveling as much as he did, he had never made many close friends. He had people that he occassionally heard from, but no one quite like Charlie Bradbury. He had only been here a couple months and this woman was trying to convince him to stick around, to do him a huge favor. He had tried to up and leave them all, and she wasn't angry at all. He smiled to himself.

"Charlie, I don't know what to say. Thank you, for this and for everything. I cannot express how much your friendship means to me, especially considering I was afraid I had fucked it up." He heard her chuckle on the other end of the line, "I will give him a call. Thanks Charlie."

He hung up the phone, swiping a hand over his face before getting up to pack his things.

**Notes for the Chapter:**

> Well guys, I think we are nearing the end here. I'm not sure just how much is left, but I'm hoping everyone enjoys where this goes!  
> Thanks again for all your kind words and kudos, even when I'm slow to update. You are all so, SO appreciated!


	36. Chapter 36

Naturally, Sam and Dean ended up at a bar in in the late afternoon. Dean had been hoping Sam's never ending run-ins with every person at the office would deter him from the inevitable conversation, but as he sipped his beer he could feel Sam watching, analyzing. 

"What?" he glared, wiping foam from his lip.

Sam ducked his head, and Dean was sure they were both equally unsure how to start. "I just want to make sure you're okay, man." Sam said, lifting his eyes back to Dean's.

With a sigh, Dean went in for a larger helping of beer, before slumping back into the booth.

"I don't know, Sammy. It just seems like I can't ever get a win. I thought after things with Benny… I don't know. It took me a while to get back on my feet after, now it looks like it was just to get knocked back on my ass." He wouldn't look at Sam, eyes focused on the ceiling above the booth while his fingers traced idly through the condensation on his glass. "I thought things would be better, because, I mean, how could they be _worse_?"

"It's not worse, Dean, I think it's just a… slight derailment. I saw the way you two were that day on video chat, I've heard the way you smile when you talk about him. I think it just needs to settle, and then you can speak with him. It will work out."

At this, Dean squinted across to Sam. His little brother had never been the type to make false promises and tell him what he wanted to hear, so if this is what Sammy really thought, well then maybe he just needed to grow a pair and deal with it.

"So what do I do?" Dean asked, downing the rest of his beer and flagging the waiter for another.

Sam huffed a laugh, "Dude, I'm not a psychic, I don't know. But if it were me, I'd give the guy a call-" he stopped short, raising his eyebrows as he watched Dean accept a new beer and down more than half of it in almost the same motion, "-maybe when you're, uh, not trying to break any drinking records."

Dean smirked then, eager to change the subject. "You used to be able to keep up," he gestured at Sam's mostly full glass. Sam's eyes narrowed, accepting the challenge, catching up without missing a beat.

A few hours later, they realized they were maybe getting too old for trying to go drink for drink. Especially on a Monday night.

 

***

 

Dean had decided on Tuesday morning that he was taking some time off to spend with Sam, and it definitely had nothing to do with his monster of a hangover. Luckily, dragging Sam on some Seattle themed adventures had taken both their minds off Cas for the time being.

Wednesday, however, Dean wasn't so lucky. He woke up reaching across the bed, grasping at empty sheets before he felt a hollowness settle in his gut. Reluctantly opening his eyes, his impulse was to text Cas that he missed waking up to him as he did on days they didn't sleep at each other's homes. His body clock demanding that he stay awake, Dean decided to drag himself on a run, and he slipped outside into the surprisingly warm air. 

He was running, his mind flipping through ideas of what to do with Sam today, before he even realized where he was headed. As he rounded the corner to Cas's street, he slowed, hoping maybe to catch a glimpse of morning activity through the studio windows. Dean let out a sigh when he realized they were dark. He thought about sucking it up, going to knock on the door and beg to explain, or even calling him now, but with a glance at his watch he remembered he was the only insane person out this early. 

As Dean continued up the road, out of habit he glanced to the nearby parking lot in search of Cas's car, and felt the pit in his stomach grow ever larger as he realized it wasn't there. So, he was gone then. Out of town maybe, or moved on to somewhere new like he had mentioned all those months ago. He shook his head, willing himself to believe that Cas would have at least said goodbye first. Dean thought back to when things with Benny had first gone south, the anger and hatred, and how he had no interest in seeing the man ever again, and he wondered if that was how he had made Cas feel. 

Pushing himself harder on the run back to his place, he contemplated his next move. He couldn't bear the thought of Cas feeling the way he had felt. He wanted Cas to know that it was a misunderstanding, that he was wrong for never telling him, that he wanted him back, permanently if he could. 

The thought scared him, but not as much as the thought of just letting Cas go. Taking a breath, he typed out a quick message to Cas, then threw his phone to the bed and headed for the shower.

_'I'm sorry.'_

**Notes for the Chapter:**

> Thank you guys for being so incredibly patient and supportive of all this! I'm working towards an ending, promise, I've just always been bad at conclusions so it's slow going. Here's this to hold you over until I get more that I feel good about! xo

**Author's Note:**

> This is my first go at writing something like this. Tips and tricks are appreciated. Bear with me!
> 
> I don't have a regular posting schedule because I don't have a regular writing schedule, but I always put up 2-3 chapter at a time to make up for the long waits in between. I had never intended for this to be so long, but I hope it's enjoyable!


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